Get ready to journey through one of America’s most breathtakingly diverse states. From the storybook charm and world-class wines of the Willamette Valley, to Portland’s electric creativity and culture, Oregon is where every traveler finds their rhythm. Stand in awe beneath the snow-capped majesty of Mount Hood, wander the windswept cliffs of the rugged Pacific Coast, and chase waterfalls through the dramatic Columbia River Gorge.
Whether you're sipping Pinot in a vineyard, hiking through ancient forests, or exploring vibrant city streets, Oregon stirs the soul and awakens your sense of wonder. Come see why Oregon truly has it all.
Your Oregon adventure begins in the storybook town of McMinnville, nestled in the heart of the world-renowned Willamette Valley. Today is all about unwinding and soaking in the charm of your surroundings. Let the pace slow as you settle in— sip a glass of local Pinot, breathe in the vineyard air, and let the journey begin. If you’re feeling refreshed, take a leisurely stroll through downtown McMinnville, where historic buildings, cozy cafés, boutique shops, and acclaimed restaurants line the charming main street. It's the perfect introduction to Oregon’s unique blend of rustic elegance and small-town soul.
You made it- welcome to Oregon!
After landing at Portland International Airport, collect your luggage then make your way to the rental car center. Retrieve your rental car and say goodbye to Portland for now - don't worry, you'll be back!
McMinnville is one of the Willamette Valley's most charming towns, with many locally owned boutiques, coffee shops, and restaurants. Build in time during your three-night stay to wander around and explore it.
Many tasting rooms in McMinnville offer the best wines in the Willamette Valley. One of the best is R. Stuart & Co. Tasting Room. The wines are excellent with servers who are friendly and very knowledgeable. Be sure to order the warm rosemary cashews!
Today, you’ll visit three outstanding wineries, each offering not only remarkable wines but also sweeping vineyard views and warm hospitality. Sip, swirl, and savor as you discover what makes this valley a must-visit for wine lovers around the globe.
Cheers to a day of taste and tranquility!
The first stop on your Oregon wine trail is the beautiful Abbey Road Farm. The impeccably manicured lawn and grounds will greet you as soon as you arrive. Have your wine tasting out on the terrace, enjoying views of rolling vineyards. Abbey Road Farm offers traditional Willamette Valley varietals, such as Pinot Noir, as well as unique offerings like Trousseau Noir and Aligoté. On a hot day, try the Sparkling Rosé, with notes of strawberry and a deliciously crisp, refreshing finish.
Just a short drive from Abbey Road Farm is Dominio IV Wines. Located on a farm that dates to the mid-19th century, Dominio IV fittingly offers wine tastings in your choice of the century-old barn or the farmhouse. The experience at this winery is relaxing and peaceful.
By this point, you have almost certainly worked up an appetite! After you leave Dominio IV Wines, drive 5 minutes west on NE Hendricks Road and arrive in the quaint town of Carlton. There are many great restaurants here, and one of the best is Carlton Bakery. This cafe offers a full coffee bar, sandwiches, quiches, and numerous baked treats perfect for enjoying on the road or for breakfast the next day. A local favorite is the Sea Biscuit, made with cardamom, black sesame, and pearl sugar. Carlton Bakery also has a selection of locally-produced products such as chocolate hazelnut butter, honey, and olive oil.
The final winery for the day is Coeur De Terre Vineyard back in McMinnville. Coeur De Terre produces quintessential Willamette Valley Wines using sustainable and organic practices. You'll enjoy your wine in their cozy tasting room and learn about the terrain and grape blocks that the vintages are sourced from. After you finish your tasting, the rest of the day is yours to explore! If you haven't done so already, wander around downtown McMinnville and grab dinner at one of the local restaurants.
Today, you will discover Oregon's rugged Pacific coast with a scenic road trip. There are two options for your journey today: one shorter trip and one extended trip if you are feeling adventurous! On your route, you'll discover lush forests of fir, hemlock, and spruce trees that nearly touch the sea. Explore tranquil beaches and peaceful coves while marveling at Oregon's giant rock formations. In addition to the natural wonders, enjoy authentic local goods to fully immerse yourself in the coastal experience.
The first stop on your road trip is Cape Lookout State Park. For hiking enthusiasts, consider the Cape Trail, which winds through forests with ocean views to the tip of Cape Lookout and back. This hike is approximately 5 miles round-trip. A family-friendly option is the Nature Trail. This is a short walk to the beach with a lovely view of Cape Lookout and the neighboring trees. As you leave Cape Lookout State Park, continue north on the Three Capes Scenic Route, which has numerous points with stunning views of the Pacific Ocean.
For a taste of the Pacific Ocean (literally!), stop into the seaside shop of Jacobsen Salt Co. Jacobsen Salt Co. harvests salt from water in the nearby Netarts Bay. In the gift shop, you can buy an array of salty products, including cooking salt, spices, and sweets. They also sell sustainably-produced honey. Don't leave without buying a box of their divine salted caramels!
Continue your journey north along the Three Capes Scenic Route until you reach the idyllic town of Oceanside. Oceanside Beach offers incredible views of the coast and of Three Arch Rocks National Wildlife Refuge. As you walk along the sea, you'll find a tunnel in one of the cliffs that leads to another scenic spot, Agate Beach.
After exploring Oceanside Beach, grab a bite to eat at Roseanna's Cafe where locally-sourced seafood is served with an unbeatable sea view. Order the clam chowder and surfer sandwich with a mini baguette. Don't forget to finish your meal with some marionberry cobbler, a true Oregon staple!
You now have two options for your journey:
- For a shorter route, travel through the town of Tillamook. Tillamook is home to the famous Tillamook Creamery. Tours and free cheese tastings are offered here, but it is very touristy. Continue your journey east for a scenic drive through Tillamook State Forest. From there, you'll head south back towards McMinnville.
- For a longer route with more coastal views, continue your journey by heading north from Tillamook on US-101 N towards Arch Cape.
Arch Cape is a peaceful community between Manzanita and the famous Cannon Beach. A walk along the beach of Arch Cape reveals staggering cliffs and a beautiful view of the impressive Castle Rock. Oswald West State Park is nearby and has beautiful seaside hikes and vistas.
After leaving Arch Cape, drive north on US-101 N and arrive to Oregon's most famous beach. Cannon Beach is very picturesque with stunning views of its crown jewel, Haystack Rock. This coastline is breathtaking so it is no wonder that in 2013, Cannon Beach ranked among National Geographic's top 100 most beautiful places. Given this accolade, it can be quite touristy but is beautiful to experience.
After a fulfilling day of coastal exploration, it is time to head home.
Today, it’s time to return to the vibrant city of Portland, where creative energy meets laid-back charm. As Oregon’s largest city, Portland surprises visitors with its welcoming, small-town feel wrapped in a cosmopolitan setting. With a thriving arts scene, renowned festivals, and a culinary reputation that draws food lovers from around the world, this West Coast gem has something for everyone.
Known as the Rose City, Portland will delight you with numerous lush landscapes and signature gardens. Your day includes discovering highlights of the lively Downtown District, where tree-lined streets lead to artisan shops, local cafés, and iconic cultural landmarks. You’ll find moments of calm in a serene garden oasis just minutes from the city center, then dive into the creative soul of Oregon through handcrafted goods and a visit to the legendary Powell’s City of Books, the largest independent bookstore on Earth.
The Portland Japanese Garden is a serene escape located in Portland's Washington Park. The park opened in 1967 as an authentic Japanese garden and has since developed into a beloved destination for tourists and locals alike. Features of the property include Japanese trees, water fountains, and a traditional Zen garden. Find tranquility as you wander along the garden's walking paths and bridges. Enjoy the peaceful waterfall, known as Heavenly Falls, as colorful koi fish swim below in the Strolling Pond Garden.
A short walk below the Portland Japanese Garden is the International Rose Test Garden. Walking through this space feels as though you've wandered into a fairy tale. This beautiful property is truly enchanting and is a delight to see and smell. The garden is home to more than 10,000 rose bushes and over 600 varieties. If there was ever a time to stop and smell the roses, now is that moment. Entry to the garden is free; however, the Portland Rose Society does accept donations to help maintain the park.
If you're getting hungry, take a break to enjoy some local eats! One of the best places to do so is in the Nob Hill Neighborhood. Kells Brewery in Nob Hill is a Portland institution that is a brewery and traditional Irish pub. You'll find a variety of in-house brews at Kells as well as an expansive food menu.
Kells is conveniently close to Portland's Providence Park, home of the Portland Timbers soccer team. If the Timbers are playing during your stay, book tickets to a game! It's a great way to feel like a local.
A trip to Portland must include a visit to the expansive Powell's City of Books. Powell's is the largest independently-owned bookstore in the world and really feels like a city of its own. The book collection at Powell's is truly impressive and feels limitless. Both new and used books are available for purchase, and there is also a cafe here, so you can fully submerge in a good read. Be sure to visit the Rare Books Room before you leave!
After Powell's City of Books, walk through downtown Portland to discover artisan shops and their selection of locally crafted goods. Stores offering products from Oregon-based vendors include MadeHere, Amity Artisan Goods, and Tender Loving Empire. Another great way to explore local artisans is to visit the Portland Saturday Market.
If you're done shopping and ready for a refreshing beverage, stop by Oregon Wines on Broadway to enjoy a variety of wines from the Willamette Valley and Oregon.
Today you’ll venture beyond downtown to discover the colorful neighborhoods that give Portland its character and charm. Each district offers its own personality, from tree-lined streets and eclectic shops to vibrant murals and cozy cafés. As you explore, you’ll visit a remarkable park where thoughtful design and natural beauty come together in perfect balance, offering a peaceful retreat within the city’s reach. Your journey continues with a visit to a serene public space devoted to nature and quiet reflection— a place where spirituality and landscape blend seamlessly. As the day winds down, you’ll experience Portland the way locals do, sampling flavors from the city’s beloved food carts, known for serving up everything from global street food to Pacific Northwest favorites. And of course, no Portland evening is complete without a sweet treat to top it all off.
The first destination of day is the beautiful Cathedral Park. This park is a short drive north of downtown Portland and sits long the Willamette River. The most impressive feature of the park is St. Johns Bridge whose substructures have quite the cathedral-like design. In addition to the beauty of the bridge, you'll find nature patches through the park that are home to local plants and gardens that support native pollinators. This is a peaceful place to sip a morning coffee, read a book or simply enjoy the surroundings.
After finishing at Cathedral Park, drive east to Portland's Madison South neighborhood to visit The Grotto. This outdoor sanctuary is a Catholic place of prayer but is open to all who seek a peaceful retreat surrounded by nature. The property has over 60 acres of greenspace and is home to a chapels, gardens and an active monastery.
Portland is home to many fine-dining restaurants but you'd be remiss to visit without experiencing the famous food cart scene. Across the city, you'll find hubs of food carts serving ecclectic fare from all over the world. One of best places to enjoy this casual dining experience is at Hawthorne Asylum in the Hawthorne District. Other highly-reviewed food cart hubs include Cartopia (also in the Hawthorne District) and Hinterland Bar & Carts in Southeast Portland.
Portland is home to an abundance of local ice cream shops to satisfy your sweet tooth. The most famous of these is Salt & Straw, which has multiple locations across the city and offers both traditional and unique ice cream flavors. A smaller ice cream shop worth a visit is Cloud City Ice Cream in Southeast Portland. Cloud City produces small-batch ice cream made with local ingredients. For a unique Oregon treat, try the lemon black pepper marionberry jam flavor.
In addition to world-class wine, Oregon has a very impressive microbrewery scene. There are over 80 of these local establishments in the Portland area. Hopworks Brewery - Powell Mothership is an excellent choice for locally brewed, sustainably crafted beer. Purchase beer by the glass or order a flight to try a variety of their brews. For a snack, try the Beer Time Pretzels with beer cheese. You can also join in on axe-throwing if you're looking for a fun challenge!
Today you’ll leave the city behind and head northeast from Portland, following the dramatic curves of the Columbia River Gorge— a natural masterpiece carved by time and framed by towering cliffs, lush forests, and cascading waterfalls. Along this breathtaking route, you’ll encounter some of Oregon’s most iconic and untouched falls, each one offering a moment of awe and serenity.
As the journey unfolds, you’ll stop in a charming riverside town that blends small-town warmth with scenic beauty, perfect for a relaxing stroll or a quiet cup of coffee with a view. To finish the day, you’ll visit a local orchard where the air is sweet with the scent of ripening fruit. Here, you can pick seasonal produce straight from the trees and enjoy handcrafted cider made right on site. It’s a day that blends Oregon’s natural grandeur with its agricultural heart, leaving you refreshed and inspired.
Our first destination along the Columbia River Gorge is Wahkeena Falls. Wahkeena Falls is a beautiful cascade that reaches over 240 feet. The walk to the base of the falls is easy; however, if you would like an excellent view, take a moderate hike up the left side of the falls, approximately 5-10 minutes. The pathway is rocky, so appropriate shoes should be worn. A longer 2.8-mile round-trip hike is also an option to reach an arched stone bridge crossing under the falls. This route is moderate to difficult in skill level.
A short drive north of Waheena Falls is the famous Multnomah Falls. At over 600 feet in height, Multnomah Falls is Oregon's tallest and most famous waterfall. This area is quite popular with tourists, so the parking lot at Multnomah Falls often fills up early in the day. If this is the case, consider visiting on your return journey as it is much less crowded in the afternoon.
The base of the falls is easy to access and gives a great view of the waterfall and of the arched Benson Bridge. For an easy-to-moderate difficulty walk, take the paved path to the right of the falls, which will take you directly to the bridge for a closer view. A longer hike (2.4 miles round-trip) to the top of the falls offers a quieter experience.
Continue along your journey to arrive at the picturesque Horsetail Falls which measures approximately 180 feet in height. The walk to the base of the waterfall is quite easy from the parking lot. On a warm day, take a dip in the natural pool underneath.
After finishing at Horsetail Falls, drive east along the scenic I-84 E to Bridge of the Gods. This nearly century-old bridge connects Oregon to Washington and crosses over the Columbia River. The bridge serves as a toll road but is open to pedestrian traffic for those without a fear of heights.
Park at the base of the bridge for an incredible view of the Columbia River Gorge. You may also find local vendors here selling goods such as fresh fruit and locally caught salmon.
The next stop along your journey is the cozy town of Hood River, Oregon. If you'd like to venture into the Columbia River, consider a kayak or paddleboard rental at Hood River Waterfront Park. Grab lunch at one of the riverfront restaurants to try a wide variety of in-house beers as well as food using locally-sourced ingredients. After lunch, wander around the town of Hood River to find a souvenir at a local art gallery, bookstore, or clothing store.
Your final stop for the day is The Gorge White House. This historic farm has been operating since the early 20th century. Today, The Gorge White House offers seasonal U-pick fruit and flowers as well as in-house ciders and wines. Pause here to pick what's in season or to enjoy a refreshing beverage before returning to Portland for the evening.
If you’re eager to see more of Mount Hood, today brings the perfect opportunity to get even closer to Oregon’s most iconic peak. Traveling east, you’ll venture deeper into the wilderness, where the landscape opens up to reveal ever more stunning views of the mountain’s snow-dusted summit.
Your journey begins with a visit to a locally-owned farm tucked away in the forested hills, where you’ll meet friendly animals and enjoy the warm, welcoming spirit of Oregon’s rural heartland. As the road winds on, you’ll arrive at a peaceful alpine lake—an ideal setting for a quiet picnic surrounded by tall trees and tranquil waters. The day concludes with a stop at a historic mountain lodge nestled at the base of Mount Hood, where stone walls and timber beams tell stories of decades past. Here, you'll stand face-to-face with Oregon’s tallest mountain, a breathtaking finale to a day filled with natural wonder, simple pleasures, and unforgettable views.
The first stop of the day is a tour at Highland Farms located in Brightwood, Oregon. On your tour, get up close and personal with the farm's friendly animals including Highland cows, sheep and birds. Follow your host along the forest trail for a peaceful walk as you learn about the property and the animals.
After Highland Farms, drive east along US-26 E to Trillium Lake. This public land includes a lake with incredible views of Mount Hood, campgrounds, and a hiking trail. Stop and enjoy a picnic just steps from the water. The Trillium Lake Loop is an easy walking trail that circles around the lake for a 360° view. Kayak rentals are also available for a gentle row across the water.
The final stop for the day is Timberline Lodge, a historic hotel constructed in 1937. In the ski season, Timberline operates as a ski lodge for winter sports enthusiasts. During the warmer months, the lodge remains open and is a great place to see Mount Hood up close. For the best view, grab a drink at Ram's Head Bar & Restaurant. After you've had your fill of beautiful views and a tasty drink, start your journey back to Portland for your final night in the Rose City.
It's time to say goodbye to Oregon and to return home. Hopefully, there are thoughtful souvenirs that will travel with you. More importantly, however, you will bring home fond memories of this incredible state. Oregon's wild beauty will forever hold a special place in your heart.
After arriving back at the Portland International Airport, return your rental car, then enter the main lobby. After you pass the check-in area, take a few minutes to appreciate the beautiful design of this airport. In true Oregon fashion, every corner is thoughtfully planned. If you missed out on any local souvenirs, there are many Oregon-based shops with locations in the airport, such as Pendletons, Made in Oregon, Tender Loving Empire, and even another branch of Powell's Books.
Have a safe journey home!
As your Oregon adventure comes to a close, take a moment to reflect on the richness of the journey. From the rolling vineyards of the Willamette Valley to the creative pulse of Portland, from misty coastal shores to mountain peaks that touch the sky, you’ve experienced the many faces of this extraordinary state. Along the way, you’ve tasted world-class wine, wandered through ancient forests, stood beside thunderous waterfalls, and connected with the stories and people that make Oregon so unique. This journey has offered both peaceful retreats and unforgettable moments of discovery—a perfect blend of rest, adventure, and inspiration. As you head home, you’ll carry not only memories, but a lasting sense of Oregon’s magic and its invitation to return.
Get ready to journey through one of America’s most breathtakingly diverse states. From the storybook charm and world-class wines of the Willamette Valley, to Portland’s electric creativity and culture, Oregon is where every traveler finds their rhythm. Stand in awe beneath the snow-capped majesty of Mount Hood, wander the windswept cliffs of the rugged Pacific Coast, and chase waterfalls through the dramatic Columbia River Gorge.
Whether you're sipping Pinot in a vineyard, hiking through ancient forests, or exploring vibrant city streets, Oregon stirs the soul and awakens your sense of wonder. Come see why Oregon truly has it all.
Your Oregon adventure begins in the storybook town of McMinnville, nestled in the heart of the world-renowned Willamette Valley. Today is all about unwinding and soaking in the charm of your surroundings. Let the pace slow as you settle in— sip a glass of local Pinot, breathe in the vineyard air, and let the journey begin. If you’re feeling refreshed, take a leisurely stroll through downtown McMinnville, where historic buildings, cozy cafés, boutique shops, and acclaimed restaurants line the charming main street. It's the perfect introduction to Oregon’s unique blend of rustic elegance and small-town soul.
You made it- welcome to Oregon!
After landing at Portland International Airport, collect your luggage then make your way to the rental car center. Retrieve your rental car and say goodbye to Portland for now - don't worry, you'll be back!
McMinnville is one of the Willamette Valley's most charming towns, with many locally owned boutiques, coffee shops, and restaurants. Build in time during your three-night stay to wander around and explore it.
Many tasting rooms in McMinnville offer the best wines in the Willamette Valley. One of the best is R. Stuart & Co. Tasting Room. The wines are excellent with servers who are friendly and very knowledgeable. Be sure to order the warm rosemary cashews!
Today, you’ll visit three outstanding wineries, each offering not only remarkable wines but also sweeping vineyard views and warm hospitality. Sip, swirl, and savor as you discover what makes this valley a must-visit for wine lovers around the globe.
Cheers to a day of taste and tranquility!
The first stop on your Oregon wine trail is the beautiful Abbey Road Farm. The impeccably manicured lawn and grounds will greet you as soon as you arrive. Have your wine tasting out on the terrace, enjoying views of rolling vineyards. Abbey Road Farm offers traditional Willamette Valley varietals, such as Pinot Noir, as well as unique offerings like Trousseau Noir and Aligoté. On a hot day, try the Sparkling Rosé, with notes of strawberry and a deliciously crisp, refreshing finish.
Just a short drive from Abbey Road Farm is Dominio IV Wines. Located on a farm that dates to the mid-19th century, Dominio IV fittingly offers wine tastings in your choice of the century-old barn or the farmhouse. The experience at this winery is relaxing and peaceful.
By this point, you have almost certainly worked up an appetite! After you leave Dominio IV Wines, drive 5 minutes west on NE Hendricks Road and arrive in the quaint town of Carlton. There are many great restaurants here, and one of the best is Carlton Bakery. This cafe offers a full coffee bar, sandwiches, quiches, and numerous baked treats perfect for enjoying on the road or for breakfast the next day. A local favorite is the Sea Biscuit, made with cardamom, black sesame, and pearl sugar. Carlton Bakery also has a selection of locally-produced products such as chocolate hazelnut butter, honey, and olive oil.
The final winery for the day is Coeur De Terre Vineyard back in McMinnville. Coeur De Terre produces quintessential Willamette Valley Wines using sustainable and organic practices. You'll enjoy your wine in their cozy tasting room and learn about the terrain and grape blocks that the vintages are sourced from. After you finish your tasting, the rest of the day is yours to explore! If you haven't done so already, wander around downtown McMinnville and grab dinner at one of the local restaurants.
Today, you will discover Oregon's rugged Pacific coast with a scenic road trip. There are two options for your journey today: one shorter trip and one extended trip if you are feeling adventurous! On your route, you'll discover lush forests of fir, hemlock, and spruce trees that nearly touch the sea. Explore tranquil beaches and peaceful coves while marveling at Oregon's giant rock formations. In addition to the natural wonders, enjoy authentic local goods to fully immerse yourself in the coastal experience.
The first stop on your road trip is Cape Lookout State Park. For hiking enthusiasts, consider the Cape Trail, which winds through forests with ocean views to the tip of Cape Lookout and back. This hike is approximately 5 miles round-trip. A family-friendly option is the Nature Trail. This is a short walk to the beach with a lovely view of Cape Lookout and the neighboring trees. As you leave Cape Lookout State Park, continue north on the Three Capes Scenic Route, which has numerous points with stunning views of the Pacific Ocean.
For a taste of the Pacific Ocean (literally!), stop into the seaside shop of Jacobsen Salt Co. Jacobsen Salt Co. harvests salt from water in the nearby Netarts Bay. In the gift shop, you can buy an array of salty products, including cooking salt, spices, and sweets. They also sell sustainably-produced honey. Don't leave without buying a box of their divine salted caramels!
Continue your journey north along the Three Capes Scenic Route until you reach the idyllic town of Oceanside. Oceanside Beach offers incredible views of the coast and of Three Arch Rocks National Wildlife Refuge. As you walk along the sea, you'll find a tunnel in one of the cliffs that leads to another scenic spot, Agate Beach.
After exploring Oceanside Beach, grab a bite to eat at Roseanna's Cafe where locally-sourced seafood is served with an unbeatable sea view. Order the clam chowder and surfer sandwich with a mini baguette. Don't forget to finish your meal with some marionberry cobbler, a true Oregon staple!
You now have two options for your journey:
- For a shorter route, travel through the town of Tillamook. Tillamook is home to the famous Tillamook Creamery. Tours and free cheese tastings are offered here, but it is very touristy. Continue your journey east for a scenic drive through Tillamook State Forest. From there, you'll head south back towards McMinnville.
- For a longer route with more coastal views, continue your journey by heading north from Tillamook on US-101 N towards Arch Cape.
Arch Cape is a peaceful community between Manzanita and the famous Cannon Beach. A walk along the beach of Arch Cape reveals staggering cliffs and a beautiful view of the impressive Castle Rock. Oswald West State Park is nearby and has beautiful seaside hikes and vistas.
After leaving Arch Cape, drive north on US-101 N and arrive to Oregon's most famous beach. Cannon Beach is very picturesque with stunning views of its crown jewel, Haystack Rock. This coastline is breathtaking so it is no wonder that in 2013, Cannon Beach ranked among National Geographic's top 100 most beautiful places. Given this accolade, it can be quite touristy but is beautiful to experience.
After a fulfilling day of coastal exploration, it is time to head home.
Today, it’s time to return to the vibrant city of Portland, where creative energy meets laid-back charm. As Oregon’s largest city, Portland surprises visitors with its welcoming, small-town feel wrapped in a cosmopolitan setting. With a thriving arts scene, renowned festivals, and a culinary reputation that draws food lovers from around the world, this West Coast gem has something for everyone.
Known as the Rose City, Portland will delight you with numerous lush landscapes and signature gardens. Your day includes discovering highlights of the lively Downtown District, where tree-lined streets lead to artisan shops, local cafés, and iconic cultural landmarks. You’ll find moments of calm in a serene garden oasis just minutes from the city center, then dive into the creative soul of Oregon through handcrafted goods and a visit to the legendary Powell’s City of Books, the largest independent bookstore on Earth.
The Portland Japanese Garden is a serene escape located in Portland's Washington Park. The park opened in 1967 as an authentic Japanese garden and has since developed into a beloved destination for tourists and locals alike. Features of the property include Japanese trees, water fountains, and a traditional Zen garden. Find tranquility as you wander along the garden's walking paths and bridges. Enjoy the peaceful waterfall, known as Heavenly Falls, as colorful koi fish swim below in the Strolling Pond Garden.
A short walk below the Portland Japanese Garden is the International Rose Test Garden. Walking through this space feels as though you've wandered into a fairy tale. This beautiful property is truly enchanting and is a delight to see and smell. The garden is home to more than 10,000 rose bushes and over 600 varieties. If there was ever a time to stop and smell the roses, now is that moment. Entry to the garden is free; however, the Portland Rose Society does accept donations to help maintain the park.
If you're getting hungry, take a break to enjoy some local eats! One of the best places to do so is in the Nob Hill Neighborhood. Kells Brewery in Nob Hill is a Portland institution that is a brewery and traditional Irish pub. You'll find a variety of in-house brews at Kells as well as an expansive food menu.
Kells is conveniently close to Portland's Providence Park, home of the Portland Timbers soccer team. If the Timbers are playing during your stay, book tickets to a game! It's a great way to feel like a local.
A trip to Portland must include a visit to the expansive Powell's City of Books. Powell's is the largest independently-owned bookstore in the world and really feels like a city of its own. The book collection at Powell's is truly impressive and feels limitless. Both new and used books are available for purchase, and there is also a cafe here, so you can fully submerge in a good read. Be sure to visit the Rare Books Room before you leave!
After Powell's City of Books, walk through downtown Portland to discover artisan shops and their selection of locally crafted goods. Stores offering products from Oregon-based vendors include MadeHere, Amity Artisan Goods, and Tender Loving Empire. Another great way to explore local artisans is to visit the Portland Saturday Market.
If you're done shopping and ready for a refreshing beverage, stop by Oregon Wines on Broadway to enjoy a variety of wines from the Willamette Valley and Oregon.
Today you’ll venture beyond downtown to discover the colorful neighborhoods that give Portland its character and charm. Each district offers its own personality, from tree-lined streets and eclectic shops to vibrant murals and cozy cafés. As you explore, you’ll visit a remarkable park where thoughtful design and natural beauty come together in perfect balance, offering a peaceful retreat within the city’s reach. Your journey continues with a visit to a serene public space devoted to nature and quiet reflection— a place where spirituality and landscape blend seamlessly. As the day winds down, you’ll experience Portland the way locals do, sampling flavors from the city’s beloved food carts, known for serving up everything from global street food to Pacific Northwest favorites. And of course, no Portland evening is complete without a sweet treat to top it all off.
The first destination of day is the beautiful Cathedral Park. This park is a short drive north of downtown Portland and sits long the Willamette River. The most impressive feature of the park is St. Johns Bridge whose substructures have quite the cathedral-like design. In addition to the beauty of the bridge, you'll find nature patches through the park that are home to local plants and gardens that support native pollinators. This is a peaceful place to sip a morning coffee, read a book or simply enjoy the surroundings.
After finishing at Cathedral Park, drive east to Portland's Madison South neighborhood to visit The Grotto. This outdoor sanctuary is a Catholic place of prayer but is open to all who seek a peaceful retreat surrounded by nature. The property has over 60 acres of greenspace and is home to a chapels, gardens and an active monastery.
Portland is home to many fine-dining restaurants but you'd be remiss to visit without experiencing the famous food cart scene. Across the city, you'll find hubs of food carts serving ecclectic fare from all over the world. One of best places to enjoy this casual dining experience is at Hawthorne Asylum in the Hawthorne District. Other highly-reviewed food cart hubs include Cartopia (also in the Hawthorne District) and Hinterland Bar & Carts in Southeast Portland.
Portland is home to an abundance of local ice cream shops to satisfy your sweet tooth. The most famous of these is Salt & Straw, which has multiple locations across the city and offers both traditional and unique ice cream flavors. A smaller ice cream shop worth a visit is Cloud City Ice Cream in Southeast Portland. Cloud City produces small-batch ice cream made with local ingredients. For a unique Oregon treat, try the lemon black pepper marionberry jam flavor.
In addition to world-class wine, Oregon has a very impressive microbrewery scene. There are over 80 of these local establishments in the Portland area. Hopworks Brewery - Powell Mothership is an excellent choice for locally brewed, sustainably crafted beer. Purchase beer by the glass or order a flight to try a variety of their brews. For a snack, try the Beer Time Pretzels with beer cheese. You can also join in on axe-throwing if you're looking for a fun challenge!
Today you’ll leave the city behind and head northeast from Portland, following the dramatic curves of the Columbia River Gorge— a natural masterpiece carved by time and framed by towering cliffs, lush forests, and cascading waterfalls. Along this breathtaking route, you’ll encounter some of Oregon’s most iconic and untouched falls, each one offering a moment of awe and serenity.
As the journey unfolds, you’ll stop in a charming riverside town that blends small-town warmth with scenic beauty, perfect for a relaxing stroll or a quiet cup of coffee with a view. To finish the day, you’ll visit a local orchard where the air is sweet with the scent of ripening fruit. Here, you can pick seasonal produce straight from the trees and enjoy handcrafted cider made right on site. It’s a day that blends Oregon’s natural grandeur with its agricultural heart, leaving you refreshed and inspired.
Our first destination along the Columbia River Gorge is Wahkeena Falls. Wahkeena Falls is a beautiful cascade that reaches over 240 feet. The walk to the base of the falls is easy; however, if you would like an excellent view, take a moderate hike up the left side of the falls, approximately 5-10 minutes. The pathway is rocky, so appropriate shoes should be worn. A longer 2.8-mile round-trip hike is also an option to reach an arched stone bridge crossing under the falls. This route is moderate to difficult in skill level.
A short drive north of Waheena Falls is the famous Multnomah Falls. At over 600 feet in height, Multnomah Falls is Oregon's tallest and most famous waterfall. This area is quite popular with tourists, so the parking lot at Multnomah Falls often fills up early in the day. If this is the case, consider visiting on your return journey as it is much less crowded in the afternoon.
The base of the falls is easy to access and gives a great view of the waterfall and of the arched Benson Bridge. For an easy-to-moderate difficulty walk, take the paved path to the right of the falls, which will take you directly to the bridge for a closer view. A longer hike (2.4 miles round-trip) to the top of the falls offers a quieter experience.
Continue along your journey to arrive at the picturesque Horsetail Falls which measures approximately 180 feet in height. The walk to the base of the waterfall is quite easy from the parking lot. On a warm day, take a dip in the natural pool underneath.
After finishing at Horsetail Falls, drive east along the scenic I-84 E to Bridge of the Gods. This nearly century-old bridge connects Oregon to Washington and crosses over the Columbia River. The bridge serves as a toll road but is open to pedestrian traffic for those without a fear of heights.
Park at the base of the bridge for an incredible view of the Columbia River Gorge. You may also find local vendors here selling goods such as fresh fruit and locally caught salmon.
The next stop along your journey is the cozy town of Hood River, Oregon. If you'd like to venture into the Columbia River, consider a kayak or paddleboard rental at Hood River Waterfront Park. Grab lunch at one of the riverfront restaurants to try a wide variety of in-house beers as well as food using locally-sourced ingredients. After lunch, wander around the town of Hood River to find a souvenir at a local art gallery, bookstore, or clothing store.
Your final stop for the day is The Gorge White House. This historic farm has been operating since the early 20th century. Today, The Gorge White House offers seasonal U-pick fruit and flowers as well as in-house ciders and wines. Pause here to pick what's in season or to enjoy a refreshing beverage before returning to Portland for the evening.
If you’re eager to see more of Mount Hood, today brings the perfect opportunity to get even closer to Oregon’s most iconic peak. Traveling east, you’ll venture deeper into the wilderness, where the landscape opens up to reveal ever more stunning views of the mountain’s snow-dusted summit.
Your journey begins with a visit to a locally-owned farm tucked away in the forested hills, where you’ll meet friendly animals and enjoy the warm, welcoming spirit of Oregon’s rural heartland. As the road winds on, you’ll arrive at a peaceful alpine lake—an ideal setting for a quiet picnic surrounded by tall trees and tranquil waters. The day concludes with a stop at a historic mountain lodge nestled at the base of Mount Hood, where stone walls and timber beams tell stories of decades past. Here, you'll stand face-to-face with Oregon’s tallest mountain, a breathtaking finale to a day filled with natural wonder, simple pleasures, and unforgettable views.
The first stop of the day is a tour at Highland Farms located in Brightwood, Oregon. On your tour, get up close and personal with the farm's friendly animals including Highland cows, sheep and birds. Follow your host along the forest trail for a peaceful walk as you learn about the property and the animals.
After Highland Farms, drive east along US-26 E to Trillium Lake. This public land includes a lake with incredible views of Mount Hood, campgrounds, and a hiking trail. Stop and enjoy a picnic just steps from the water. The Trillium Lake Loop is an easy walking trail that circles around the lake for a 360° view. Kayak rentals are also available for a gentle row across the water.
The final stop for the day is Timberline Lodge, a historic hotel constructed in 1937. In the ski season, Timberline operates as a ski lodge for winter sports enthusiasts. During the warmer months, the lodge remains open and is a great place to see Mount Hood up close. For the best view, grab a drink at Ram's Head Bar & Restaurant. After you've had your fill of beautiful views and a tasty drink, start your journey back to Portland for your final night in the Rose City.
It's time to say goodbye to Oregon and to return home. Hopefully, there are thoughtful souvenirs that will travel with you. More importantly, however, you will bring home fond memories of this incredible state. Oregon's wild beauty will forever hold a special place in your heart.
After arriving back at the Portland International Airport, return your rental car, then enter the main lobby. After you pass the check-in area, take a few minutes to appreciate the beautiful design of this airport. In true Oregon fashion, every corner is thoughtfully planned. If you missed out on any local souvenirs, there are many Oregon-based shops with locations in the airport, such as Pendletons, Made in Oregon, Tender Loving Empire, and even another branch of Powell's Books.
Have a safe journey home!
As your Oregon adventure comes to a close, take a moment to reflect on the richness of the journey. From the rolling vineyards of the Willamette Valley to the creative pulse of Portland, from misty coastal shores to mountain peaks that touch the sky, you’ve experienced the many faces of this extraordinary state. Along the way, you’ve tasted world-class wine, wandered through ancient forests, stood beside thunderous waterfalls, and connected with the stories and people that make Oregon so unique. This journey has offered both peaceful retreats and unforgettable moments of discovery—a perfect blend of rest, adventure, and inspiration. As you head home, you’ll carry not only memories, but a lasting sense of Oregon’s magic and its invitation to return.
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itinerary by Carolyn Turner
Get ready to journey through one of America’s most breathtakingly diverse states. From the storybook charm and world-class wines of the Willamette Valley, to Portland’s electric creativity and culture, Oregon is where every traveler finds their rhythm. Stand in awe beneath the snow-capped majesty of Mount Hood, wander the windswept cliffs of the rugged Pacific Coast, and chase waterfalls through the dramatic Columbia River Gorge.
Whether you're sipping Pinot in a vineyard, hiking through ancient forests, or exploring vibrant city streets, Oregon stirs the soul and awakens your sense of wonder. Come see why Oregon truly has it all.
Your Oregon adventure begins in the storybook town of McMinnville, nestled in the heart of the world-renowned Willamette Valley. Today is all about unwinding and soaking in the charm of your surroundings. Let the pace slow as you settle in— sip a glass of local Pinot, breathe in the vineyard air, and let the journey begin. If you’re feeling refreshed, take a leisurely stroll through downtown McMinnville, where historic buildings, cozy cafés, boutique shops, and acclaimed restaurants line the charming main street. It's the perfect introduction to Oregon’s unique blend of rustic elegance and small-town soul.
You made it- welcome to Oregon!
After landing at Portland International Airport, collect your luggage then make your way to the rental car center. Retrieve your rental car and say goodbye to Portland for now - don't worry, you'll be back!
McMinnville is one of the Willamette Valley's most charming towns, with many locally owned boutiques, coffee shops, and restaurants. Build in time during your three-night stay to wander around and explore it.
Many tasting rooms in McMinnville offer the best wines in the Willamette Valley. One of the best is R. Stuart & Co. Tasting Room. The wines are excellent with servers who are friendly and very knowledgeable. Be sure to order the warm rosemary cashews!
Today, you’ll visit three outstanding wineries, each offering not only remarkable wines but also sweeping vineyard views and warm hospitality. Sip, swirl, and savor as you discover what makes this valley a must-visit for wine lovers around the globe.
Cheers to a day of taste and tranquility!
The first stop on your Oregon wine trail is the beautiful Abbey Road Farm. The impeccably manicured lawn and grounds will greet you as soon as you arrive. Have your wine tasting out on the terrace, enjoying views of rolling vineyards. Abbey Road Farm offers traditional Willamette Valley varietals, such as Pinot Noir, as well as unique offerings like Trousseau Noir and Aligoté. On a hot day, try the Sparkling Rosé, with notes of strawberry and a deliciously crisp, refreshing finish.
Just a short drive from Abbey Road Farm is Dominio IV Wines. Located on a farm that dates to the mid-19th century, Dominio IV fittingly offers wine tastings in your choice of the century-old barn or the farmhouse. The experience at this winery is relaxing and peaceful.
By this point, you have almost certainly worked up an appetite! After you leave Dominio IV Wines, drive 5 minutes west on NE Hendricks Road and arrive in the quaint town of Carlton. There are many great restaurants here, and one of the best is Carlton Bakery. This cafe offers a full coffee bar, sandwiches, quiches, and numerous baked treats perfect for enjoying on the road or for breakfast the next day. A local favorite is the Sea Biscuit, made with cardamom, black sesame, and pearl sugar. Carlton Bakery also has a selection of locally-produced products such as chocolate hazelnut butter, honey, and olive oil.
The final winery for the day is Coeur De Terre Vineyard back in McMinnville. Coeur De Terre produces quintessential Willamette Valley Wines using sustainable and organic practices. You'll enjoy your wine in their cozy tasting room and learn about the terrain and grape blocks that the vintages are sourced from. After you finish your tasting, the rest of the day is yours to explore! If you haven't done so already, wander around downtown McMinnville and grab dinner at one of the local restaurants.
Today, you will discover Oregon's rugged Pacific coast with a scenic road trip. There are two options for your journey today: one shorter trip and one extended trip if you are feeling adventurous! On your route, you'll discover lush forests of fir, hemlock, and spruce trees that nearly touch the sea. Explore tranquil beaches and peaceful coves while marveling at Oregon's giant rock formations. In addition to the natural wonders, enjoy authentic local goods to fully immerse yourself in the coastal experience.
The first stop on your road trip is Cape Lookout State Park. For hiking enthusiasts, consider the Cape Trail, which winds through forests with ocean views to the tip of Cape Lookout and back. This hike is approximately 5 miles round-trip. A family-friendly option is the Nature Trail. This is a short walk to the beach with a lovely view of Cape Lookout and the neighboring trees. As you leave Cape Lookout State Park, continue north on the Three Capes Scenic Route, which has numerous points with stunning views of the Pacific Ocean.
For a taste of the Pacific Ocean (literally!), stop into the seaside shop of Jacobsen Salt Co. Jacobsen Salt Co. harvests salt from water in the nearby Netarts Bay. In the gift shop, you can buy an array of salty products, including cooking salt, spices, and sweets. They also sell sustainably-produced honey. Don't leave without buying a box of their divine salted caramels!
Continue your journey north along the Three Capes Scenic Route until you reach the idyllic town of Oceanside. Oceanside Beach offers incredible views of the coast and of Three Arch Rocks National Wildlife Refuge. As you walk along the sea, you'll find a tunnel in one of the cliffs that leads to another scenic spot, Agate Beach.
After exploring Oceanside Beach, grab a bite to eat at Roseanna's Cafe where locally-sourced seafood is served with an unbeatable sea view. Order the clam chowder and surfer sandwich with a mini baguette. Don't forget to finish your meal with some marionberry cobbler, a true Oregon staple!
You now have two options for your journey:
- For a shorter route, travel through the town of Tillamook. Tillamook is home to the famous Tillamook Creamery. Tours and free cheese tastings are offered here, but it is very touristy. Continue your journey east for a scenic drive through Tillamook State Forest. From there, you'll head south back towards McMinnville.
- For a longer route with more coastal views, continue your journey by heading north from Tillamook on US-101 N towards Arch Cape.
Arch Cape is a peaceful community between Manzanita and the famous Cannon Beach. A walk along the beach of Arch Cape reveals staggering cliffs and a beautiful view of the impressive Castle Rock. Oswald West State Park is nearby and has beautiful seaside hikes and vistas.
After leaving Arch Cape, drive north on US-101 N and arrive to Oregon's most famous beach. Cannon Beach is very picturesque with stunning views of its crown jewel, Haystack Rock. This coastline is breathtaking so it is no wonder that in 2013, Cannon Beach ranked among National Geographic's top 100 most beautiful places. Given this accolade, it can be quite touristy but is beautiful to experience.
After a fulfilling day of coastal exploration, it is time to head home.
Today, it’s time to return to the vibrant city of Portland, where creative energy meets laid-back charm. As Oregon’s largest city, Portland surprises visitors with its welcoming, small-town feel wrapped in a cosmopolitan setting. With a thriving arts scene, renowned festivals, and a culinary reputation that draws food lovers from around the world, this West Coast gem has something for everyone.
Known as the Rose City, Portland will delight you with numerous lush landscapes and signature gardens. Your day includes discovering highlights of the lively Downtown District, where tree-lined streets lead to artisan shops, local cafés, and iconic cultural landmarks. You’ll find moments of calm in a serene garden oasis just minutes from the city center, then dive into the creative soul of Oregon through handcrafted goods and a visit to the legendary Powell’s City of Books, the largest independent bookstore on Earth.
The Portland Japanese Garden is a serene escape located in Portland's Washington Park. The park opened in 1967 as an authentic Japanese garden and has since developed into a beloved destination for tourists and locals alike. Features of the property include Japanese trees, water fountains, and a traditional Zen garden. Find tranquility as you wander along the garden's walking paths and bridges. Enjoy the peaceful waterfall, known as Heavenly Falls, as colorful koi fish swim below in the Strolling Pond Garden.
A short walk below the Portland Japanese Garden is the International Rose Test Garden. Walking through this space feels as though you've wandered into a fairy tale. This beautiful property is truly enchanting and is a delight to see and smell. The garden is home to more than 10,000 rose bushes and over 600 varieties. If there was ever a time to stop and smell the roses, now is that moment. Entry to the garden is free; however, the Portland Rose Society does accept donations to help maintain the park.
If you're getting hungry, take a break to enjoy some local eats! One of the best places to do so is in the Nob Hill Neighborhood. Kells Brewery in Nob Hill is a Portland institution that is a brewery and traditional Irish pub. You'll find a variety of in-house brews at Kells as well as an expansive food menu.
Kells is conveniently close to Portland's Providence Park, home of the Portland Timbers soccer team. If the Timbers are playing during your stay, book tickets to a game! It's a great way to feel like a local.
A trip to Portland must include a visit to the expansive Powell's City of Books. Powell's is the largest independently-owned bookstore in the world and really feels like a city of its own. The book collection at Powell's is truly impressive and feels limitless. Both new and used books are available for purchase, and there is also a cafe here, so you can fully submerge in a good read. Be sure to visit the Rare Books Room before you leave!
After Powell's City of Books, walk through downtown Portland to discover artisan shops and their selection of locally crafted goods. Stores offering products from Oregon-based vendors include MadeHere, Amity Artisan Goods, and Tender Loving Empire. Another great way to explore local artisans is to visit the Portland Saturday Market.
If you're done shopping and ready for a refreshing beverage, stop by Oregon Wines on Broadway to enjoy a variety of wines from the Willamette Valley and Oregon.
Today you’ll venture beyond downtown to discover the colorful neighborhoods that give Portland its character and charm. Each district offers its own personality, from tree-lined streets and eclectic shops to vibrant murals and cozy cafés. As you explore, you’ll visit a remarkable park where thoughtful design and natural beauty come together in perfect balance, offering a peaceful retreat within the city’s reach. Your journey continues with a visit to a serene public space devoted to nature and quiet reflection— a place where spirituality and landscape blend seamlessly. As the day winds down, you’ll experience Portland the way locals do, sampling flavors from the city’s beloved food carts, known for serving up everything from global street food to Pacific Northwest favorites. And of course, no Portland evening is complete without a sweet treat to top it all off.
The first destination of day is the beautiful Cathedral Park. This park is a short drive north of downtown Portland and sits long the Willamette River. The most impressive feature of the park is St. Johns Bridge whose substructures have quite the cathedral-like design. In addition to the beauty of the bridge, you'll find nature patches through the park that are home to local plants and gardens that support native pollinators. This is a peaceful place to sip a morning coffee, read a book or simply enjoy the surroundings.
After finishing at Cathedral Park, drive east to Portland's Madison South neighborhood to visit The Grotto. This outdoor sanctuary is a Catholic place of prayer but is open to all who seek a peaceful retreat surrounded by nature. The property has over 60 acres of greenspace and is home to a chapels, gardens and an active monastery.
Portland is home to many fine-dining restaurants but you'd be remiss to visit without experiencing the famous food cart scene. Across the city, you'll find hubs of food carts serving ecclectic fare from all over the world. One of best places to enjoy this casual dining experience is at Hawthorne Asylum in the Hawthorne District. Other highly-reviewed food cart hubs include Cartopia (also in the Hawthorne District) and Hinterland Bar & Carts in Southeast Portland.
Portland is home to an abundance of local ice cream shops to satisfy your sweet tooth. The most famous of these is Salt & Straw, which has multiple locations across the city and offers both traditional and unique ice cream flavors. A smaller ice cream shop worth a visit is Cloud City Ice Cream in Southeast Portland. Cloud City produces small-batch ice cream made with local ingredients. For a unique Oregon treat, try the lemon black pepper marionberry jam flavor.
In addition to world-class wine, Oregon has a very impressive microbrewery scene. There are over 80 of these local establishments in the Portland area. Hopworks Brewery - Powell Mothership is an excellent choice for locally brewed, sustainably crafted beer. Purchase beer by the glass or order a flight to try a variety of their brews. For a snack, try the Beer Time Pretzels with beer cheese. You can also join in on axe-throwing if you're looking for a fun challenge!
Today you’ll leave the city behind and head northeast from Portland, following the dramatic curves of the Columbia River Gorge— a natural masterpiece carved by time and framed by towering cliffs, lush forests, and cascading waterfalls. Along this breathtaking route, you’ll encounter some of Oregon’s most iconic and untouched falls, each one offering a moment of awe and serenity.
As the journey unfolds, you’ll stop in a charming riverside town that blends small-town warmth with scenic beauty, perfect for a relaxing stroll or a quiet cup of coffee with a view. To finish the day, you’ll visit a local orchard where the air is sweet with the scent of ripening fruit. Here, you can pick seasonal produce straight from the trees and enjoy handcrafted cider made right on site. It’s a day that blends Oregon’s natural grandeur with its agricultural heart, leaving you refreshed and inspired.
Our first destination along the Columbia River Gorge is Wahkeena Falls. Wahkeena Falls is a beautiful cascade that reaches over 240 feet. The walk to the base of the falls is easy; however, if you would like an excellent view, take a moderate hike up the left side of the falls, approximately 5-10 minutes. The pathway is rocky, so appropriate shoes should be worn. A longer 2.8-mile round-trip hike is also an option to reach an arched stone bridge crossing under the falls. This route is moderate to difficult in skill level.
A short drive north of Waheena Falls is the famous Multnomah Falls. At over 600 feet in height, Multnomah Falls is Oregon's tallest and most famous waterfall. This area is quite popular with tourists, so the parking lot at Multnomah Falls often fills up early in the day. If this is the case, consider visiting on your return journey as it is much less crowded in the afternoon.
The base of the falls is easy to access and gives a great view of the waterfall and of the arched Benson Bridge. For an easy-to-moderate difficulty walk, take the paved path to the right of the falls, which will take you directly to the bridge for a closer view. A longer hike (2.4 miles round-trip) to the top of the falls offers a quieter experience.
Continue along your journey to arrive at the picturesque Horsetail Falls which measures approximately 180 feet in height. The walk to the base of the waterfall is quite easy from the parking lot. On a warm day, take a dip in the natural pool underneath.
After finishing at Horsetail Falls, drive east along the scenic I-84 E to Bridge of the Gods. This nearly century-old bridge connects Oregon to Washington and crosses over the Columbia River. The bridge serves as a toll road but is open to pedestrian traffic for those without a fear of heights.
Park at the base of the bridge for an incredible view of the Columbia River Gorge. You may also find local vendors here selling goods such as fresh fruit and locally caught salmon.
The next stop along your journey is the cozy town of Hood River, Oregon. If you'd like to venture into the Columbia River, consider a kayak or paddleboard rental at Hood River Waterfront Park. Grab lunch at one of the riverfront restaurants to try a wide variety of in-house beers as well as food using locally-sourced ingredients. After lunch, wander around the town of Hood River to find a souvenir at a local art gallery, bookstore, or clothing store.
Your final stop for the day is The Gorge White House. This historic farm has been operating since the early 20th century. Today, The Gorge White House offers seasonal U-pick fruit and flowers as well as in-house ciders and wines. Pause here to pick what's in season or to enjoy a refreshing beverage before returning to Portland for the evening.
If you’re eager to see more of Mount Hood, today brings the perfect opportunity to get even closer to Oregon’s most iconic peak. Traveling east, you’ll venture deeper into the wilderness, where the landscape opens up to reveal ever more stunning views of the mountain’s snow-dusted summit.
Your journey begins with a visit to a locally-owned farm tucked away in the forested hills, where you’ll meet friendly animals and enjoy the warm, welcoming spirit of Oregon’s rural heartland. As the road winds on, you’ll arrive at a peaceful alpine lake—an ideal setting for a quiet picnic surrounded by tall trees and tranquil waters. The day concludes with a stop at a historic mountain lodge nestled at the base of Mount Hood, where stone walls and timber beams tell stories of decades past. Here, you'll stand face-to-face with Oregon’s tallest mountain, a breathtaking finale to a day filled with natural wonder, simple pleasures, and unforgettable views.
The first stop of the day is a tour at Highland Farms located in Brightwood, Oregon. On your tour, get up close and personal with the farm's friendly animals including Highland cows, sheep and birds. Follow your host along the forest trail for a peaceful walk as you learn about the property and the animals.
After Highland Farms, drive east along US-26 E to Trillium Lake. This public land includes a lake with incredible views of Mount Hood, campgrounds, and a hiking trail. Stop and enjoy a picnic just steps from the water. The Trillium Lake Loop is an easy walking trail that circles around the lake for a 360° view. Kayak rentals are also available for a gentle row across the water.
The final stop for the day is Timberline Lodge, a historic hotel constructed in 1937. In the ski season, Timberline operates as a ski lodge for winter sports enthusiasts. During the warmer months, the lodge remains open and is a great place to see Mount Hood up close. For the best view, grab a drink at Ram's Head Bar & Restaurant. After you've had your fill of beautiful views and a tasty drink, start your journey back to Portland for your final night in the Rose City.
It's time to say goodbye to Oregon and to return home. Hopefully, there are thoughtful souvenirs that will travel with you. More importantly, however, you will bring home fond memories of this incredible state. Oregon's wild beauty will forever hold a special place in your heart.
After arriving back at the Portland International Airport, return your rental car, then enter the main lobby. After you pass the check-in area, take a few minutes to appreciate the beautiful design of this airport. In true Oregon fashion, every corner is thoughtfully planned. If you missed out on any local souvenirs, there are many Oregon-based shops with locations in the airport, such as Pendletons, Made in Oregon, Tender Loving Empire, and even another branch of Powell's Books.
Have a safe journey home!
As your Oregon adventure comes to a close, take a moment to reflect on the richness of the journey. From the rolling vineyards of the Willamette Valley to the creative pulse of Portland, from misty coastal shores to mountain peaks that touch the sky, you’ve experienced the many faces of this extraordinary state. Along the way, you’ve tasted world-class wine, wandered through ancient forests, stood beside thunderous waterfalls, and connected with the stories and people that make Oregon so unique. This journey has offered both peaceful retreats and unforgettable moments of discovery—a perfect blend of rest, adventure, and inspiration. As you head home, you’ll carry not only memories, but a lasting sense of Oregon’s magic and its invitation to return.
Get ready to journey through one of America’s most breathtakingly diverse states. From the storybook charm and world-class wines of the Willamette Valley, to Portland’s electric creativity and culture, Oregon is where every traveler finds their rhythm. Stand in awe beneath the snow-capped majesty of Mount Hood, wander the windswept cliffs of the rugged Pacific Coast, and chase waterfalls through the dramatic Columbia River Gorge.
Whether you're sipping Pinot in a vineyard, hiking through ancient forests, or exploring vibrant city streets, Oregon stirs the soul and awakens your sense of wonder. Come see why Oregon truly has it all.
Your Oregon adventure begins in the storybook town of McMinnville, nestled in the heart of the world-renowned Willamette Valley. Today is all about unwinding and soaking in the charm of your surroundings. Let the pace slow as you settle in— sip a glass of local Pinot, breathe in the vineyard air, and let the journey begin. If you’re feeling refreshed, take a leisurely stroll through downtown McMinnville, where historic buildings, cozy cafés, boutique shops, and acclaimed restaurants line the charming main street. It's the perfect introduction to Oregon’s unique blend of rustic elegance and small-town soul.
You made it- welcome to Oregon!
After landing at Portland International Airport, collect your luggage then make your way to the rental car center. Retrieve your rental car and say goodbye to Portland for now - don't worry, you'll be back!
McMinnville is one of the Willamette Valley's most charming towns, with many locally owned boutiques, coffee shops, and restaurants. Build in time during your three-night stay to wander around and explore it.
Many tasting rooms in McMinnville offer the best wines in the Willamette Valley. One of the best is R. Stuart & Co. Tasting Room. The wines are excellent with servers who are friendly and very knowledgeable. Be sure to order the warm rosemary cashews!
Today, you’ll visit three outstanding wineries, each offering not only remarkable wines but also sweeping vineyard views and warm hospitality. Sip, swirl, and savor as you discover what makes this valley a must-visit for wine lovers around the globe.
Cheers to a day of taste and tranquility!
The first stop on your Oregon wine trail is the beautiful Abbey Road Farm. The impeccably manicured lawn and grounds will greet you as soon as you arrive. Have your wine tasting out on the terrace, enjoying views of rolling vineyards. Abbey Road Farm offers traditional Willamette Valley varietals, such as Pinot Noir, as well as unique offerings like Trousseau Noir and Aligoté. On a hot day, try the Sparkling Rosé, with notes of strawberry and a deliciously crisp, refreshing finish.
Just a short drive from Abbey Road Farm is Dominio IV Wines. Located on a farm that dates to the mid-19th century, Dominio IV fittingly offers wine tastings in your choice of the century-old barn or the farmhouse. The experience at this winery is relaxing and peaceful.
By this point, you have almost certainly worked up an appetite! After you leave Dominio IV Wines, drive 5 minutes west on NE Hendricks Road and arrive in the quaint town of Carlton. There are many great restaurants here, and one of the best is Carlton Bakery. This cafe offers a full coffee bar, sandwiches, quiches, and numerous baked treats perfect for enjoying on the road or for breakfast the next day. A local favorite is the Sea Biscuit, made with cardamom, black sesame, and pearl sugar. Carlton Bakery also has a selection of locally-produced products such as chocolate hazelnut butter, honey, and olive oil.
The final winery for the day is Coeur De Terre Vineyard back in McMinnville. Coeur De Terre produces quintessential Willamette Valley Wines using sustainable and organic practices. You'll enjoy your wine in their cozy tasting room and learn about the terrain and grape blocks that the vintages are sourced from. After you finish your tasting, the rest of the day is yours to explore! If you haven't done so already, wander around downtown McMinnville and grab dinner at one of the local restaurants.
Today, you will discover Oregon's rugged Pacific coast with a scenic road trip. There are two options for your journey today: one shorter trip and one extended trip if you are feeling adventurous! On your route, you'll discover lush forests of fir, hemlock, and spruce trees that nearly touch the sea. Explore tranquil beaches and peaceful coves while marveling at Oregon's giant rock formations. In addition to the natural wonders, enjoy authentic local goods to fully immerse yourself in the coastal experience.
The first stop on your road trip is Cape Lookout State Park. For hiking enthusiasts, consider the Cape Trail, which winds through forests with ocean views to the tip of Cape Lookout and back. This hike is approximately 5 miles round-trip. A family-friendly option is the Nature Trail. This is a short walk to the beach with a lovely view of Cape Lookout and the neighboring trees. As you leave Cape Lookout State Park, continue north on the Three Capes Scenic Route, which has numerous points with stunning views of the Pacific Ocean.
For a taste of the Pacific Ocean (literally!), stop into the seaside shop of Jacobsen Salt Co. Jacobsen Salt Co. harvests salt from water in the nearby Netarts Bay. In the gift shop, you can buy an array of salty products, including cooking salt, spices, and sweets. They also sell sustainably-produced honey. Don't leave without buying a box of their divine salted caramels!
Continue your journey north along the Three Capes Scenic Route until you reach the idyllic town of Oceanside. Oceanside Beach offers incredible views of the coast and of Three Arch Rocks National Wildlife Refuge. As you walk along the sea, you'll find a tunnel in one of the cliffs that leads to another scenic spot, Agate Beach.
After exploring Oceanside Beach, grab a bite to eat at Roseanna's Cafe where locally-sourced seafood is served with an unbeatable sea view. Order the clam chowder and surfer sandwich with a mini baguette. Don't forget to finish your meal with some marionberry cobbler, a true Oregon staple!
You now have two options for your journey:
- For a shorter route, travel through the town of Tillamook. Tillamook is home to the famous Tillamook Creamery. Tours and free cheese tastings are offered here, but it is very touristy. Continue your journey east for a scenic drive through Tillamook State Forest. From there, you'll head south back towards McMinnville.
- For a longer route with more coastal views, continue your journey by heading north from Tillamook on US-101 N towards Arch Cape.
Arch Cape is a peaceful community between Manzanita and the famous Cannon Beach. A walk along the beach of Arch Cape reveals staggering cliffs and a beautiful view of the impressive Castle Rock. Oswald West State Park is nearby and has beautiful seaside hikes and vistas.
After leaving Arch Cape, drive north on US-101 N and arrive to Oregon's most famous beach. Cannon Beach is very picturesque with stunning views of its crown jewel, Haystack Rock. This coastline is breathtaking so it is no wonder that in 2013, Cannon Beach ranked among National Geographic's top 100 most beautiful places. Given this accolade, it can be quite touristy but is beautiful to experience.
After a fulfilling day of coastal exploration, it is time to head home.
Today, it’s time to return to the vibrant city of Portland, where creative energy meets laid-back charm. As Oregon’s largest city, Portland surprises visitors with its welcoming, small-town feel wrapped in a cosmopolitan setting. With a thriving arts scene, renowned festivals, and a culinary reputation that draws food lovers from around the world, this West Coast gem has something for everyone.
Known as the Rose City, Portland will delight you with numerous lush landscapes and signature gardens. Your day includes discovering highlights of the lively Downtown District, where tree-lined streets lead to artisan shops, local cafés, and iconic cultural landmarks. You’ll find moments of calm in a serene garden oasis just minutes from the city center, then dive into the creative soul of Oregon through handcrafted goods and a visit to the legendary Powell’s City of Books, the largest independent bookstore on Earth.
The Portland Japanese Garden is a serene escape located in Portland's Washington Park. The park opened in 1967 as an authentic Japanese garden and has since developed into a beloved destination for tourists and locals alike. Features of the property include Japanese trees, water fountains, and a traditional Zen garden. Find tranquility as you wander along the garden's walking paths and bridges. Enjoy the peaceful waterfall, known as Heavenly Falls, as colorful koi fish swim below in the Strolling Pond Garden.
A short walk below the Portland Japanese Garden is the International Rose Test Garden. Walking through this space feels as though you've wandered into a fairy tale. This beautiful property is truly enchanting and is a delight to see and smell. The garden is home to more than 10,000 rose bushes and over 600 varieties. If there was ever a time to stop and smell the roses, now is that moment. Entry to the garden is free; however, the Portland Rose Society does accept donations to help maintain the park.
If you're getting hungry, take a break to enjoy some local eats! One of the best places to do so is in the Nob Hill Neighborhood. Kells Brewery in Nob Hill is a Portland institution that is a brewery and traditional Irish pub. You'll find a variety of in-house brews at Kells as well as an expansive food menu.
Kells is conveniently close to Portland's Providence Park, home of the Portland Timbers soccer team. If the Timbers are playing during your stay, book tickets to a game! It's a great way to feel like a local.
A trip to Portland must include a visit to the expansive Powell's City of Books. Powell's is the largest independently-owned bookstore in the world and really feels like a city of its own. The book collection at Powell's is truly impressive and feels limitless. Both new and used books are available for purchase, and there is also a cafe here, so you can fully submerge in a good read. Be sure to visit the Rare Books Room before you leave!
After Powell's City of Books, walk through downtown Portland to discover artisan shops and their selection of locally crafted goods. Stores offering products from Oregon-based vendors include MadeHere, Amity Artisan Goods, and Tender Loving Empire. Another great way to explore local artisans is to visit the Portland Saturday Market.
If you're done shopping and ready for a refreshing beverage, stop by Oregon Wines on Broadway to enjoy a variety of wines from the Willamette Valley and Oregon.
Today you’ll venture beyond downtown to discover the colorful neighborhoods that give Portland its character and charm. Each district offers its own personality, from tree-lined streets and eclectic shops to vibrant murals and cozy cafés. As you explore, you’ll visit a remarkable park where thoughtful design and natural beauty come together in perfect balance, offering a peaceful retreat within the city’s reach. Your journey continues with a visit to a serene public space devoted to nature and quiet reflection— a place where spirituality and landscape blend seamlessly. As the day winds down, you’ll experience Portland the way locals do, sampling flavors from the city’s beloved food carts, known for serving up everything from global street food to Pacific Northwest favorites. And of course, no Portland evening is complete without a sweet treat to top it all off.
The first destination of day is the beautiful Cathedral Park. This park is a short drive north of downtown Portland and sits long the Willamette River. The most impressive feature of the park is St. Johns Bridge whose substructures have quite the cathedral-like design. In addition to the beauty of the bridge, you'll find nature patches through the park that are home to local plants and gardens that support native pollinators. This is a peaceful place to sip a morning coffee, read a book or simply enjoy the surroundings.
After finishing at Cathedral Park, drive east to Portland's Madison South neighborhood to visit The Grotto. This outdoor sanctuary is a Catholic place of prayer but is open to all who seek a peaceful retreat surrounded by nature. The property has over 60 acres of greenspace and is home to a chapels, gardens and an active monastery.
Portland is home to many fine-dining restaurants but you'd be remiss to visit without experiencing the famous food cart scene. Across the city, you'll find hubs of food carts serving ecclectic fare from all over the world. One of best places to enjoy this casual dining experience is at Hawthorne Asylum in the Hawthorne District. Other highly-reviewed food cart hubs include Cartopia (also in the Hawthorne District) and Hinterland Bar & Carts in Southeast Portland.
Portland is home to an abundance of local ice cream shops to satisfy your sweet tooth. The most famous of these is Salt & Straw, which has multiple locations across the city and offers both traditional and unique ice cream flavors. A smaller ice cream shop worth a visit is Cloud City Ice Cream in Southeast Portland. Cloud City produces small-batch ice cream made with local ingredients. For a unique Oregon treat, try the lemon black pepper marionberry jam flavor.
In addition to world-class wine, Oregon has a very impressive microbrewery scene. There are over 80 of these local establishments in the Portland area. Hopworks Brewery - Powell Mothership is an excellent choice for locally brewed, sustainably crafted beer. Purchase beer by the glass or order a flight to try a variety of their brews. For a snack, try the Beer Time Pretzels with beer cheese. You can also join in on axe-throwing if you're looking for a fun challenge!
Today you’ll leave the city behind and head northeast from Portland, following the dramatic curves of the Columbia River Gorge— a natural masterpiece carved by time and framed by towering cliffs, lush forests, and cascading waterfalls. Along this breathtaking route, you’ll encounter some of Oregon’s most iconic and untouched falls, each one offering a moment of awe and serenity.
As the journey unfolds, you’ll stop in a charming riverside town that blends small-town warmth with scenic beauty, perfect for a relaxing stroll or a quiet cup of coffee with a view. To finish the day, you’ll visit a local orchard where the air is sweet with the scent of ripening fruit. Here, you can pick seasonal produce straight from the trees and enjoy handcrafted cider made right on site. It’s a day that blends Oregon’s natural grandeur with its agricultural heart, leaving you refreshed and inspired.
Our first destination along the Columbia River Gorge is Wahkeena Falls. Wahkeena Falls is a beautiful cascade that reaches over 240 feet. The walk to the base of the falls is easy; however, if you would like an excellent view, take a moderate hike up the left side of the falls, approximately 5-10 minutes. The pathway is rocky, so appropriate shoes should be worn. A longer 2.8-mile round-trip hike is also an option to reach an arched stone bridge crossing under the falls. This route is moderate to difficult in skill level.
A short drive north of Waheena Falls is the famous Multnomah Falls. At over 600 feet in height, Multnomah Falls is Oregon's tallest and most famous waterfall. This area is quite popular with tourists, so the parking lot at Multnomah Falls often fills up early in the day. If this is the case, consider visiting on your return journey as it is much less crowded in the afternoon.
The base of the falls is easy to access and gives a great view of the waterfall and of the arched Benson Bridge. For an easy-to-moderate difficulty walk, take the paved path to the right of the falls, which will take you directly to the bridge for a closer view. A longer hike (2.4 miles round-trip) to the top of the falls offers a quieter experience.
Continue along your journey to arrive at the picturesque Horsetail Falls which measures approximately 180 feet in height. The walk to the base of the waterfall is quite easy from the parking lot. On a warm day, take a dip in the natural pool underneath.
After finishing at Horsetail Falls, drive east along the scenic I-84 E to Bridge of the Gods. This nearly century-old bridge connects Oregon to Washington and crosses over the Columbia River. The bridge serves as a toll road but is open to pedestrian traffic for those without a fear of heights.
Park at the base of the bridge for an incredible view of the Columbia River Gorge. You may also find local vendors here selling goods such as fresh fruit and locally caught salmon.
The next stop along your journey is the cozy town of Hood River, Oregon. If you'd like to venture into the Columbia River, consider a kayak or paddleboard rental at Hood River Waterfront Park. Grab lunch at one of the riverfront restaurants to try a wide variety of in-house beers as well as food using locally-sourced ingredients. After lunch, wander around the town of Hood River to find a souvenir at a local art gallery, bookstore, or clothing store.
Your final stop for the day is The Gorge White House. This historic farm has been operating since the early 20th century. Today, The Gorge White House offers seasonal U-pick fruit and flowers as well as in-house ciders and wines. Pause here to pick what's in season or to enjoy a refreshing beverage before returning to Portland for the evening.
If you’re eager to see more of Mount Hood, today brings the perfect opportunity to get even closer to Oregon’s most iconic peak. Traveling east, you’ll venture deeper into the wilderness, where the landscape opens up to reveal ever more stunning views of the mountain’s snow-dusted summit.
Your journey begins with a visit to a locally-owned farm tucked away in the forested hills, where you’ll meet friendly animals and enjoy the warm, welcoming spirit of Oregon’s rural heartland. As the road winds on, you’ll arrive at a peaceful alpine lake—an ideal setting for a quiet picnic surrounded by tall trees and tranquil waters. The day concludes with a stop at a historic mountain lodge nestled at the base of Mount Hood, where stone walls and timber beams tell stories of decades past. Here, you'll stand face-to-face with Oregon’s tallest mountain, a breathtaking finale to a day filled with natural wonder, simple pleasures, and unforgettable views.
The first stop of the day is a tour at Highland Farms located in Brightwood, Oregon. On your tour, get up close and personal with the farm's friendly animals including Highland cows, sheep and birds. Follow your host along the forest trail for a peaceful walk as you learn about the property and the animals.
After Highland Farms, drive east along US-26 E to Trillium Lake. This public land includes a lake with incredible views of Mount Hood, campgrounds, and a hiking trail. Stop and enjoy a picnic just steps from the water. The Trillium Lake Loop is an easy walking trail that circles around the lake for a 360° view. Kayak rentals are also available for a gentle row across the water.
The final stop for the day is Timberline Lodge, a historic hotel constructed in 1937. In the ski season, Timberline operates as a ski lodge for winter sports enthusiasts. During the warmer months, the lodge remains open and is a great place to see Mount Hood up close. For the best view, grab a drink at Ram's Head Bar & Restaurant. After you've had your fill of beautiful views and a tasty drink, start your journey back to Portland for your final night in the Rose City.
It's time to say goodbye to Oregon and to return home. Hopefully, there are thoughtful souvenirs that will travel with you. More importantly, however, you will bring home fond memories of this incredible state. Oregon's wild beauty will forever hold a special place in your heart.
After arriving back at the Portland International Airport, return your rental car, then enter the main lobby. After you pass the check-in area, take a few minutes to appreciate the beautiful design of this airport. In true Oregon fashion, every corner is thoughtfully planned. If you missed out on any local souvenirs, there are many Oregon-based shops with locations in the airport, such as Pendletons, Made in Oregon, Tender Loving Empire, and even another branch of Powell's Books.
Have a safe journey home!
As your Oregon adventure comes to a close, take a moment to reflect on the richness of the journey. From the rolling vineyards of the Willamette Valley to the creative pulse of Portland, from misty coastal shores to mountain peaks that touch the sky, you’ve experienced the many faces of this extraordinary state. Along the way, you’ve tasted world-class wine, wandered through ancient forests, stood beside thunderous waterfalls, and connected with the stories and people that make Oregon so unique. This journey has offered both peaceful retreats and unforgettable moments of discovery—a perfect blend of rest, adventure, and inspiration. As you head home, you’ll carry not only memories, but a lasting sense of Oregon’s magic and its invitation to return.
