11 Cutest Small Towns In Oregon For 2025
Looking for the best small towns to visit in Oregon in 2025? From riverside walks to exciting outdoor activities, there is something for everyone. Picture yourself walking along Astoria’s Riverwalk Trail or browsing its Sunday Market. Then, head to Hood River for kiteboarding, craft breweries, and breathtaking mountain views.
Ready to plan your trip? Keep reading to discover 11 of Oregon’s cutest small towns for your next getaway.
Ashland
Ashland blends natural surroundings, arts, and relaxation. Known for its theater scene, it hosts the Oregon Shakespeare Festival, drawing audiences from around the world with outstanding performances. In the center of town, you’ll find cafes, shops, and galleries that reflect its creative atmosphere.
For nature lovers, Lithia Park spans 93 acres with trails, ponds, and landscaped gardens. Don’t miss the sulfur water fountain, a nod to the town’s mineral-rich heritage. In winter, the Mt. Ashland Ski Area offers skiing, and during warmer months, it’s great for hiking.
For a relaxing retreat, Waterstone Spa at Lithia Springs Resort features soothing mineral water soaks. Wine enthusiasts can visit local spots like Irvine & Roberts or Weisinger Family Winery, which are known for their excellent wines and lovely views.
Astoria
Astoria combines small-town charm with a rich past and incredible views. Located at the meeting point of the Columbia River and the Pacific Ocean, it’s filled with sites to discover.
Start your visit with a trip to the Astoria Column for stunning panoramic views of the town and nearby waterways. Next, hop on the Astoria Riverfront Trolley or walk along the Riverwalk Trail for sights of the Astoria-Megler Bridge and playful sea lions. Along the trolley's route, history fans can stop at the Columbia River Maritime Museum to explore the town's rich seafaring legacy.
On Sundays, the Astoria Sunday Market features local artisans, food vendors, and crafts. Afterward, visit the Lewis and Clark National Historical Park for a picnic and insight into the explorers’ journey.
Sisters
Nestled in Central Oregon, Sisters is a charming town that offers a perfect mix of small-town warmth and outdoor adventure. Start your day with coffee and a pastry on the cozy wraparound porch at Sisters Coffee Company, then explore the Western-themed downtown filled with boutique stores, vintage shops like Hen’s Tooth, and delicious spots like The Open Door.
For nature lovers, nearby Clear Lake boasts stunning crystal-clear waters perfect for kayaking and swimming, while Lost Lake amazes visitors with its disappearing act into a volcanic sinkhole each spring. Thrill-seekers can hit the trails with a bike rental from Blazing Saddles or seek some powder at Hoodoo Ski Area.
Sisters also comes alive with events year-round, from the excitement of the Sisters Rodeo in June to the music-filled Sisters Folk Festival in October.
Jacksonville
Jacksonville, located in Southern Oregon, offers a perfect mix of history, culture, and outdoor adventures. Known for its Gold Rush past, the town is brimming with activities year-round.
Nature enthusiasts can explore the Jacksonville Woodlands Trail System, which features 16 miles of scenic paths like Beekman Woods and the Native Plant Arboretum. For water lovers, the nearby Rogue River is ideal for fishing or floating.
Wine lovers will enjoy the city’s Wine District, home to boutique wineries and tasting rooms surrounded by picturesque vineyards. In the summer, don’t miss the Britt Music & Arts Festival, an outdoor series of live performances under the stars.
History buffs can step back in time with the Jacksonville Trolley Tour or participate in the Parade of Inns in May, showcasing the town’s historic buildings. To top it all off, enjoy a delicious meal and live music at Bella Union Restaurant.
McMinnville
In the heart of Oregon’s wine country, McMinnville is a town filled with activities for all interests. With its cozy atmosphere, world-class wineries, and the quirky annual UFO Festival, there is something for everyone to discover. The UFO Festival, inspired by a famous 1950 sighting, takes place every May and draws paranormal enthusiasts with a costume parade, expert talks, live music, and alien-themed events.
Wine aficionados will appreciate the region's renowned Pinot Noir, with countless wineries in the area to visit. Try a wine tour with May Your Glass Be Filled Tours or a curated food and wine outing with Dirty Radish.
For those who love culture, the Gallery Theater hosts live performances, while the Evergreen Aviation & Space Museum showcases the legendary Spruce Goose, a colossal World War II flying boat. Nature lovers can spend time at Ed Grenfell Park, while food enthusiasts can check out artisan shops like Alchemist’s Jam & Bakery.
Manzanita
On the Oregon Coast, Manzanita is a laid-back seaside town that combines natural surroundings with a sense of calm. Known for its seven-mile beach, it’s a place where you can both relax and stay active.
Nature enthusiasts can visit Neahkahnie-Manzanita State Park or Oswald West State Park, both featuring lush forests and expansive coastal views. Hikers can climb Neahkahnie Mountain for panoramic vistas of the Pacific Ocean (keep an eye out for spouting gray whales!), while fishing enthusiasts can try their luck at the North Fork Nehalem River.
The town has a thriving arts culture. The Hoffman Center for the Arts holds workshops, performances, and film screenings and provides spaces like a clay studio and a writing lounge. Then, there is the Manzanita Art Walk, which showcases works from local creatives while bringing the community together.
Seasonal events bring an added layer of excitement to town, from festive Fourth of July gatherings to the quirky Muttzanita dog parade. Wintertime visitors can participate in the annual Polar Plunge before warming up by a cozy bonfire with fellow brave souls.
Hood River
Hood River sits along the Columbia River, providing breathtaking views of Mount Hood, Oregon's tallest mountain. This town is a hub for recreational activities. It’s especially known for windsurfing and kiteboarding, with lessons available through Kite the Gorge or kayak rentals from the Gorge Paddling Center.
Hiking enthusiasts will enjoy a serene walk to Wah Gwin Gwin Falls on the grounds of the Columbia Gorge Hotel. The Hood River Fruit Loop offers a drive or e-bike ride through approximately 30 local farms, fruit stands, flower fields, wineries, and breweries.
Take relaxation one step further with a visit to The Gorge White House. This historic farm and winery offers tastings and locally inspired bites with mountain views.
Cannon Beach
Cannon Beach is a coastal town that blends artistic culture with opportunities for outdoor exploration. Named one of America’s 100 Best Art Towns, it is home to 15 art galleries showcasing works from local and international artists. Annual art festivals, such as the Stormy Weather Arts Festival and Spring Unveiling Arts Festival, celebrate creativity and community involvement.
Public sculptures, including The Whale and The Wave, enhance the town’s streets. Haystack Rock, accessible during low tide, reveals tidepools rich with sea life. Nearby, Ecola State Park offers awe-inspiring views of the coastline and forest trails. Plus, Hug Point State Recreation Area (just 5 miles south) features sea caves that are visible during low tide.
After a day of activities, savor ocean-view clam chowder at Mo’s Seafood & Chowder or try a craft brew at Pelican Brewing.
Florence
Florence is a small coastal town filled with history and natural wonders. At its heart lies the Siuslaw River, crossed by the historic 1936 Siuslaw River Bridge, a landmark that reflects the town’s past while connecting to the present.
The Old Town district is a favorite spot, featuring shops, galleries, and locally loved eateries. Stop by Novelli's Crab and Seafood for fresh, locally sourced dishes. On Tuesdays from mid-May to mid-October, the Florence Boardwalk Market showcases crafts and food, creating a lively community gathering.
Just a short drive out, the Oregon Dunes span 40 miles, the largest sand dunes on the continent. Sandboard at Sand Master Park or take in the expansive views from North Jetty. For nature fans, the Sea Lion Caves—the largest sea cave in the US—and Darlingtonia State Natural Site, home to rare cobra lilies, are must-sees. Finally, the Heceta Head Lighthouse, perched on a coastal cliff, offers panoramic ocean views and insight into the region’s maritime heritage.
Joseph
Located near the Wallowa Mountains, Joseph is a small town known for its artistic character and rich culture. Dubbed the "Bronze Capital of Oregon," its streets showcase impressive sculptures, including a statue of Chief Joseph and a cowboy and horse, reflecting the area's creativity. The Josephy Center for Arts and Culture highlights the town’s historical and artistic roots.
Joseph is a haven for nature enthusiasts. Take the Wallowa Lake Tramway to the top of Mount Howard for breathtaking views of the surrounding landscape. For water activities, the Wallowa River is great for whitewater rafting and fly fishing. For something different, try pedaling along historic tracks with Joseph Branch Railriders.
After a day of exploring, relax at Stein Distillery, sampling locally made spirits. Whether you are drawn to its artistic charm or its outdoor recreation, Joseph provides a little something for everyone.
Brownsville
In the heart of Oregon’s Willamette Valley, Brownsville is a town steeped in history. Famous as the filming location for Stand by Me, it gives a nostalgic view of days gone by.
History buffs will appreciate landmarks like the Moyer House and the Linn County Historical Museum, located in a renovated railroad depot. The museum tells the story of early settlers and includes an exhibit on the making of Stand by Me. Don’t miss annual events like the Carriage Me Back reenactments or the Pioneer Parade, Oregon’s longest-running celebration that brings history to life.
For outdoor enthusiasts, the Over the River & Through the Woods Scenic Byway is a great spot for fall foliage, while cyclists will enjoy the Willamette Valley Scenic Bikeway. Afterward, pick up a bottle of wine from Harper's Wine House and a sandwich from Randy’s Main Street Coffee for a picnic in Pioneer Park. If you have extra time, visit the Living Rock Studios museum, a fascinating structure made from local agates, crystals, and quartz.
Oregon is packed with cute small towns that deliver big experiences. From marveling at the iconic Haystack Rock in Cannon Beach to riding historic railroad tracks in Joseph, each destination has its own story to tell. Whether you are road-tripping or looking for a quiet escape, these towns leave a lasting impression. So, pack your bags—it’s time to hit the road in 2025!
