The 12 Best Small Towns in Oregon for Historic Charm, Organic Wineries, and Adventure Treks

Stunning mountain and coastal views are also on display in Oregon's best small towns.

Portland gets all the attention in Oregon — and while the City of Roses is absolutely worth a visit for its local foodie scene, eclectic shopping, and industrial riverfront vibes, the rest of the state has even more to offer. So, we've rounded up 12 of the best small towns in Oregon with under 12,000 residents. Each one made the cut for its historic charm, delicious wineries, adventure activities, stunning mountain and coastal beauty, and more. It's time to plan your next small town getaway.


Aerial view of Astoria
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If you've seen "The Goonies," Astoria's idyllic seaside location might look familiar. Enjoy water views from the historic pedestrian corridor along the Columbia River on foot or hop on the Astoria Riverfront Trolley for a scenic ride. The downtown area is essentially one happening strip, with Oregon-focused boutiques, seafood restaurants in reclaimed canneries, and the nearby Oregon Film Museum. Buoy Beer Company and Fort George compete for the best brewery in Astoria — but the former has the ocean views.

Hood River

Sunset over Mt Hood and Hood River Valley, Oregon
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Columbia River Gorge? Check. Cascade Range? Check. Windsurfing capital of the world? Check. It must be Hood River, one of Oregon's best small towns. The Columbia River Gorge is home to some of the most magnificent waterfalls in Oregon. Trekkers, bikers, and water sports enthusiasts of all stripes gather in Hood River for outdoor adventures. If you're more into culinary experiences, the historic downtown area holds over 30 restaurants and the surrounding countryside overflows with vineyards and orchards. Hiyu Wine Farm offers gourmet fare and tours with lavish seated dinners.


A main street in Jacksonville, Oregon.
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Located on the outskirts of Medford in southern Oregon, Jacksonville is both a scenic small town and a National Historic Landmark. Gold deposits brought prosperity and settlers before Oregon officially became a state, but today, Jacksonville is better known for its yearly Britt Music & Arts Festival and plethora of antique shops. In the summer months, the Jacksonville Trolley provides a 45-minute tour of the area's unique history and architecture. Or, come in October and get the haunted version.

Cannon Beach

View of Cannon Beach, Oregon, USA
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Cannon Beach is about 90 minutes northwest of Portland, and that might explain why it draws hundreds of thousands of visitors each year. Easy access to the long, sandy shore from a plethora of family-friendly beachfront resorts and restaurants is another part of the appeal. Haystack Rock looms large over beachgoers, providing a memorable backdrop and tide pools to explore. Got a canine companion? No problem — you'll be in good company on this pet-friendly beach.


Farm and Wallowa Mountains, Powder River Valley in Joseph, Oregon
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Eastern Oregon holds another one of Oregon's best small towns: Joseph. The Wallowa Mountains backdrop earned Joseph the moniker of "Little Switzerland of America." Wallowa Lake — known for its trophy-sized fish — and Eagle Cap Wilderness hikes provide wet and dry adventure activities. In town, you'll find gear outfitters, the Wallowa County Museum, and a seasonal farmers market. Or, take a breathtaking ride on the Wallowa Lake Tramway. Four-person tram cars take you to the top of Mount Howard, where you can take in the mountain views with a glass of Willamette Valley pinot noir or a microbrew at the Summit Grill.

Baker City

Storm clouds above historic Baker City, Oregon
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Baker City is better known as the "base camp for Eastern Oregon." Sure, the area is prime for hiking, trekking, and whitewater rafting on the Snake River, but expect the unexpected here. Some sights include the Glacier 45 vodka distillery, a tiny Chinese cemetery, and the Geiser Grand Hotel that opened in 1889 and still accepts guests (and rumored ghosts).


Wood Rowboats at Dock on Clear Lake Sisters Oregon
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Sisters is on the eastern flank of the Cascade Mountains, bordered by the state's high-desert region for sunny weather through most of the year. The area is popular for rock climbing, hiking, and the eye-catching Three Sisters volcanic peaks in Deschutes National Forest. In town, expect 19th-century facades and storefronts, but decidedly modern art galleries and restaurants inside. Since 1975, Sisters has hosted the world's largest outdoor quilt show that draws thousands of visitors.


View of beautiful Yachats on the Oregon Coast, USA.
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Yachats, located on the central Oregon coast, provides intense natural beauty with modern conveniences. Pronounced yah-hots, this charming destination is tucked between the rugged coast and sprawling Siuslaw National Forest. Yachats is best explored via hiking trail or bike path. Amanda's Trail, part of the much longer Oregon Coast Trail, meanders through the forest landscape. Stop by Green Salmon Coffee Company to fuel up on fair trade coffee and vegan goodies before hitting the trail.


Hops grow in a field at Goschie Farms Inc. in Silverton, Oregon,
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Located 15 miles east of the capital city of Salem, Silverton is known as Oregon's Garden City, thanks to the Oregon Garden, which has 80 acres of flowers and parks. Don't miss the destination's plethora of murals on your way to Silver Falls State Park, known for a spectacular set of waterfalls, all visible on the Trail of Ten Falls. Architecture buffs will want to visit the Gordon House by Frank Lloyd Wright.


The town of Florence, along the Oregon Coast, USA.
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Where the central Oregon coast meets the Siuslaw River, you'll find Florence. Sea Lion Caves and Heceta Head Lighthouse are famous coastal attractions, as is the nearby Oregon Dunes National Recreation Area. Sand-crawling vehicles are a popular way to explore. The Old Town district and Siuslaw River Bridge offer local shopping and seafood eateries, like the Waterfront Depot Restaurant.

Cottage Grove

Currin covered bridge near Cottage Grove Oregon
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Cottage Grove is also known as the Covered Bridge Capital of Oregon. Check them all out on the Covered Bridges Scenic Bikeway, which starts downtown and meanders for 36 miles through agricultural and Cascade Mountain scenery. The fall foliage is especially spectacular along the route. Saginaw Vineyard and Coast Fork Brewing are both solid options for local sips and eats.


Built on a hill in the Columbia River Gorge the late afternoon sun illuminates Mosier, with highway 84 curving to the left.
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Vino enthusiasts will adore Mosier, home to Columbia River Gorge wineries. The community has three vineyards close enough that you can visit them all in one day. Analemma Wines started as a cherry farm and now has lavender fields, 10 acres of orchards and vineyards, and a tasting room. Garnier Vineyards, meanwhile, overlooks the Columbia River and cultivates rosé and pinot noir. And Idiot's Grace focuses on organic winemaking, with vineyard plots on both the Oregon and Washington sides of the river.

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