Spring in Oregon is like flipping through a vividly illustrated storybook, where every turn reveals a new, colorful adventure waiting to unfold. From artsy enclaves to adrenaline-pumping adventure hubs, the Beaver State is brimming with offbeat towns that promise an unforgettable road trip. Buckle up as we embark on a journey through eight of Oregon's most unique and captivating destinations.
Artsy Escapes In Oregon
Ashland - A Cultural Gem
Ashland isn't your average small town; it's a vibrant cultural oasis tucked away in Southern Oregon. Best known for the Oregon Shakespeare Festival, this artsy town offers more than just world-class theater. Wander through its charming streets, and you'll find a plethora of art galleries, boutique shops, and cozy delicious cafes that seem to hum with creative energy. Don't forget to take a leisurely stroll in Lithia Park, a sprawling 93-acre wonderland that serves as the town's gorgeous green heart.
Tip: Plan to spend at least an hour strolling up and down the paths in Lithia Park. The sound of trickling water from the stream will follow you wherever you go. There are plenty of bridges that cross the stream, and many shops and restaurants within walking distance of the lower end of the park where you can grab lunch or a pint.
Beyond its theatrical fame, Ashland surprises visitors with its culinary scene, ranging from cozy coffee shops to gourmet restaurants that focus on locally-sourced ingredients, (and let's not forget the nearby wineries).
The town's commitment to sustainability and community is evident in its farmers markets and the enthusiasm of its local artisans. Whether you're indulging in a farm-to-table meal or enjoying a local wine tasting, Ashland offers a blend of sensory delights that complement its artistic allure.
Make A Weekend Of It In Southern Oregon
Ashland has always been one of my favorite quirky little towns to explore and spend a day in. If you plan to spend the weekend in the area, consider spending one day in Ashland and then staying the night at the historic (and potentially haunted) Peerless Hotel. On day two, head over to Jacksonville (a 30 minute drive), which has it's own quaint charm, delicious restaurants, and interesting shops and history to explore.
Check out our full guide to Ashland here.
Cannon Beach - Where Art Meets the Ocean
Cannon Beach is a scenic masterpiece with the iconic Haystack Rock standing guard over its sandy shores. But there's more to this coastal town than breathtaking views. Cannon Beach is a haven for artists and art lovers alike, boasting an array of galleries where local and national artists showcase their work. The town's laid-back vibe is perfect for those looking to unwind, explore tide pools, and perhaps find inspiration for their next masterpiece.
Cannon Beach isn't just about the visual arts; it's a sensory feast that extends to its natural surroundings. The town's commitment to preserving its stunning landscape means that visitors can enjoy unspoiled beaches and lush state parks where outdoor activities abound.
From hiking in Ecola State Park to exploring the quaint downtown area, Cannon Beach offers a tranquil escape where nature and culture intertwine seamlessly.
Read our full guide to Cannon Beach here.
Joseph - A Canvas Of Natural And Handcrafted Beauty
Nestled in the heart of the Wallowa Mountains, Joseph is a small town with a big artistic spirit. Its main street is lined with bronze foundries and galleries that pay homage to the town's rich art scene.
Joseph's backdrop of majestic mountains and pristine lakes adds to its allure, making it a picture-perfect destination for artists and nature enthusiasts alike.
Joseph's allure is magnified by the annual festivals which bring together music, art, and local craft beers in a celebration of the town's creative spirit.
The surrounding Wallowa Lake provides a serene setting for kayaking, fishing, and even paddle boarding, making Joseph an ideal destination for those who appreciate both the beauty of the arts and the great outdoors.
Read our guide to Joseph, Oregon here.
Oregon Adventure Towns
Hood River - The Thrill-Seeker's Playground
Hood River is the epitome of an adventure town, located at the crossroads of the Columbia River Gorge and the Cascade Range. Known as the windsurfing capital of the world, it's a hotspot for not just windsurfers but also kiteboarders, mountain bikers, and hikers. Whether you're gliding on water or zip-lining through forests, Hood River guarantees an adrenaline rush with a view.
In addition to its wind and water sports, Hood River's agricultural bounty is celebrated through its wine and cider scene.
The Hood River Fruit Loop, a scenic drive through local farms and vineyards, offers a taste of the valley's rich harvests. This juxtaposition of thrilling outdoor activities and the slower pace of vineyard tours provides a balanced experience for visitors looking for both excitement and relaxation.
Read more about Hood River here, and check out our full guide to Mount Hood and all the adventures that you can have there.
Bend - Shopping And Outdoor Adventures Galore
Bend is a mecca for outdoor enthusiasts, surrounded by nature's playground. With the Deschutes River running through it and the snow-capped peaks of the Cascade Mountains nearby, Bend offers endless adventure opportunities.
From surfing (yes really, you can go surfing in Bend!) to mountain biking and stand up paddle boarding, this town has something for every thrill-seeker. And after a day full of adventure, you can unwind at one of Bend's many craft breweries.
Bend's vibrant downtown area and shopping at the Old Mill District, complements its outdoor lifestyle.
With an array of shops, galleries, and restaurants that showcase the creativity of its residents, the Old Mill District is the perfect place to spend a Saturday, or unwind after a day full of adventure.
The Deschutes River provides a stunning backdrop for the town's many festivals and events, including concerts all summer long with big name bands, the Bend Film Festival, Brewfest, Oktoberfest, and countless art shows and festivals.
Bend's unique blend of natural beauty, cultural events, and outdoor activities makes it an irresistible destination for all seasons.
Read more in our guide to Bend here.
Oakridge - A Mountain Biker's Paradise
Tucked away in the Willamette National Forest, Oakridge is often dubbed the mountain biking capital of the Pacific Northwest. With over 300 miles of singletrack trails, it's a haven for mountain bikers looking for a challenge amidst stunning natural scenery. But the adventure doesn't stop there; Oakridge also offers excellent opportunities for hiking, fishing, and soaking in hot springs.
After a day on the trails, Oakridge welcomes visitors with its down-to-earth vibe and friendly local spots where stories of the day's adventures are shared over craft beers and home-cooked meals.
Tip: One of our favorite spots to stop off in Oakridge is The 3 Legged Crane, an English style pub and restaurant.
The town's commitment to preserving its natural beauty while fostering a sense of community among outdoor enthusiasts makes Oakridge a special place where the spirit of adventure is matched by genuine hospitality.
Quaint And Quirky Oregon Towns
Sisters - Old West Charm
Sisters is a delightful blend of the old and the new, where the spirit of the Wild West meets modern-day comfort. This quaint town is famous for its annual quilt show and the Sisters Rodeo, but its charm lies in its beautifully preserved 1880s facades, boutique shops, and friendly local eateries. Sisters is also a gateway to outdoor adventures, with the Three Sisters Wilderness just a stone's throw away.
The natural beauty surrounding Sisters is a constant source of inspiration, with the majestic Cascade Mountains offering a stunning backdrop for photographers and nature lovers.
Sisters is a place where history and tradition blend with a vibrant present, making it a must-visit for those seeking an authentic Oregon experience.
Tip: Looking for a relaxing place to stay near Sisters? Try the Metolius River Resort. This gorgeous spot is on the Metolius River and features gorgeous cabins in a serene setting. Best of all, it's only a 21 minute drive from Sisters.
Read our guide to Sisters, Oregon here.
Yachats - The Hidden Coastal Jewel
Last but certainly not least, Yachats is a small coastal town that's big on personality. Often overlooked in favor of its more famous neighbors, this hidden gem offers rugged coastline views, serene forest walks, and some of the best tide pooling in Oregon. Yachats is the perfect spot for those looking to escape the hustle and bustle and immerse themselves in the tranquil beauty of Oregon's coast.
Yachats is a sanctuary for those seeking peace and natural beauty. The town's close-knit community is evident in its warm hospitality and the care taken to preserve its unique character. Annual events like the Yachats Celtic Music Festival and the Mushroom Fest celebrate the town's connection to its natural environment and artistic talents.
No trip to Yachats would be complete without taking the six minute drive south of town to check out Thor's Well and the Spouting Horn.
Whether you're watching a storm roll in from the Pacific or enjoying a sunset stroll along the Yachats River, this town offers a tranquil retreat from the typical everyday hustle, inviting visitors to slow down and savor the moment.
Read our guide to Yachats here.
Oregon's offbeat towns are the heart and soul of the state, offering a unique blend of art, adventure, and quaint charm. Whether you're an art aficionado, an adrenaline junkie, or simply in search of a peaceful retreat, these eight towns promise a road trip filled with discovery and delight.
