13 Prettiest Towns In Oregon
Oregon's prettiest towns embrace the ever-changing seasons, inviting visitors to explore nature's wonders, from blooming wildflowers in spring to vibrant fall foliage. From the windswept shores of the Pacific to the rugged beauty of the Cascade Mountains, nature is abundant wherever you go. As you journey through these prettiest towns, you will find coastal gems that offer tranquil moments against the backdrop of iconic sea stacks. Venture further inland, where historic architecture stands as a testament to the past, complemented by lively cultural festivals that celebrate the present. In the 13 prettiest towns of Oregon, beauty is an euphemism for the vivacious experiences you will have on your vacation.
Hood River
Hood River, a gem of the Columbia River Gorge, attracts adventure seekers and food lovers alike. There are plenty of exciting activities in Hood River, such as feeling the thrill of windsurfing and kitesurfing on the Columbia River's currents while surrounded by stunning scenery. Explore beautiful trails like the famous Multnomah Falls and enjoy the fresh produce from farm stands along the Hood River Fruit Loop.
Downtown Hood River welcomes visitors to explore its lively culture through art galleries such as Columbia Center For The Arts and 301 Gallery, boutiques like LaureL & EddiE, Dream Street, and Plenty, as well as farm-to-table dining options including Farm Stand in the Gorge, Celilo Restaurant & Bar, and Romuls. Guests can sample regional craft drinks, from beers to ciders, and experience the energetic vibe of the Hood River Hops Fest.
Ashland
The charming Rogue Valley is home to Ashland, one of Oregon's most captivating cities, known for the Oregon Shakespeare Festival. The festival features classics, modern plays, and an annual outdoor green show in open-air theaters that capture the spirit of the Bard.
Lithia Park serves as the centerpiece of Ashland, featuring nature trails, Japanese gardens, bubbling mineral springs, Sycamore groves, and a rose garden. Downtown Ashland is ideal for wine walks and enjoying craft brews, microbrews, ales, and wines at renowned spots like Weisinger Family Winery, Irvine & Roberts Vineyards, and Dana Campbell Vineyards. During the warmer months, the Ashland Independent Film Festival offers a variety of cinematic delights, including narrative features, documentaries, shorts, and short films.
Astoria
Astoria, where the Columbia River meets the Pacific, tells maritime tales through its captivating museums in a cozy allure. Ascend the Astoria Column for sweeping views, and explore the Columbia River Maritime Museum to uncover shipwreck stories and coastal life tales.
The Flavel House Museum offers a 19th-century experience with Queen Anne architecture, late Victorian furnishings, a winding hardwood staircase, a butler's kitchen, and classic wooden floors. Visit the Astoria-Megler Bridge for stunning sunsets and photo opportunities, and stop at Fort George Brewery for relaxing drinks like cider, wine, and beer, as well as salads and pizzas. You can also enjoy events like the Scandinavian Midsummer Festival and FisherPoets Gathering, which celebrate cultural heritage and artistic talent.
Sisters
A charming Wild West-inspired town in the Cascade Mountains, Sisters, exudes authentic Western charm and outdoor adventure. You can't help but get immersed in cowboy culture at the lively Sisters Rodeo, with broncs, bulls, and boots kicking up dirt. The Three Sisters Wilderness calls out with alpine splendor, waterfalls, rainbow trout and brook fishing, and day and night hiking trails.
Galleries like Hood Avenue Art and Raven Makes Gallery combine Western and contemporary art with Native American artisans showcasing eclectic artworks and handcrafted jewelry. The Sisters Outdoor Quilt Show and Stitchin' Post Quilt Shop decorate the town with vibrant fiber arts, quilting workshops, and crochet crafts against the stunning Cascade backdrop.
Baker City
Baker City, one of the friendliest towns in Oregon, offers a glimpse into Oregon's history with its well-preserved historic district and the Oregon Trail Interpretive Center (currently closed for renovations). If you're a cycling enthusiast, the Baker City Cycling Classic provides an exciting challenge. The 106-mile Elkhorn Scenic Byway loop begins with Elkhorn's gold rush towns along the Powder River, climbs the Blue Springs Summit, and takes you all the way to Haines.
The Anthony Lakes Ski Resort provides mountain biking, summer yurt, and camping during summer and skiing and cat trips in winter. Get in touch with Go Wild: American Adventures LLC for pack rafting, mule camping, camping, and backpacking adventures when in town.
Cottage Grove
Cottage Grove's charm comes from its historic covered bridges, like the iconic "Chambers Railroad Bridge," which offers a nostalgic glimpse. The past is not less interesting than the Cottage Grove Museum, which features Italian stained glass windows, a survivor's story from the Titanic tragedy, and the 1920 women's spring collection. The beautiful 14-mile Row River Trail is great for biking and hiking.
Cottage Grove's culture is thriving at the Cottage Theatre with performances like Rhythm & Blues, annual productions, and Roaring Twenties shows. Outdoor lovers will enjoy boating and fishing at Dorena Lake, along with regional drinks at Covered Bridge Brewery and Saginaw Vineyard. The Bohemia Mining Days festival honors the town's Gold Rush past through murals, ore cart races, movie nights, and parades.
McMinnville
McMinnville is synonymous with Oregon's wine scene, boasting numerous wineries and tasting rooms. The Evergreen Aviation & Space Museum is a highlight, showcasing the iconic Spruce Goose and other aviation marvels. Linfield University campus holds the International Pinot Noir Celebration, a must for wine lovers, featuring winery tours, walkaround tastings, and top-notch dishes.
Tice Woods offers the ideal summer afternoon experience amid an upland forest, two ponds, Baker Creek views, and a wetland. You should not overlook the fun wave pool and ten waterslides at Wings & Waves Waterpark. And there seems to be no end when it comes to wineries and vineyards. Hop on a tour to discover the best of places like Coeur De Terre Vineyard, Willamette Valley Vineyards, The Eyrie Vineyards, and R. Stuart & Co. Tasting Room.
Jacksonville
Jacksonville's beautifully preserved Gold Rush-era architecture stands as a true testament to history. The Greek Revival Beekman House Museum is a great first stop, showcasing the lifestyle of the Beekman family in the early 1900s. The Britt Music & Arts Festival celebrates music and art all summer with performances of symphony, orchestra, classical music, and country music in a natural amphitheater. You can also visit the Art Presence Art Center for regional artist exhibitions and creative classes.
The Applegate Wine Trail features 18 renowned wineries, including Cascadia Vineyards & Winery, John Michael Champagne Cellars, and Schmidt Family Vineyards, along a 50-mile route. The Victorian Christmas celebration charms with the holiday magic of carols, Christmas stories, and costume tours.
Silverton
Horticultural heritage plays a proud role at Silverton, highlighting the beautiful Oregon Garden, an 80-acre botanical haven. Here, you can stroll through a variety of plants, including daphnes, Japanese maples, and heathers, as well as themed gardens like Bosque, Conifer Garden, Axis Garden, and A-Mazing Water Garden. The town also serves as the gateway to Silver Falls State Park, home to the captivating Trail of Ten Falls, Howard Creek Horse Camp, and Smith Creek Village.
The 12 bowling lanes of the Silver Creek Lanes offer the ultimate day out with friends and family. The Oregon Garden Brewfest blends local brews and natural beauty, providing regional meads, ales, ciders, and beers. The Homer Davenport Community Festival celebrates the town's renowned cartoonist through fun races, parades, cartoon contests, and car shows.
Yachats
Your dream of a beautiful coastal vacation will be a hit on the rugged Oregon coast, where Yachats, one of the small towns to visit in Oregon, captivates with its stunning shoreline. You have many things to discover from the Pacific coastline, tide pools, and the captivating Cape Perpetua Scenic Area, showcasing the eye-catching Spouting Horn and Devil's Churn. The Amanda Trail commemorates Native American history with interpretive boards along the way. Yachats is not just famous for its seaside charm but also for its Mushrooms, which you can learn about at Yachats Village Mushroom Fest. You can explore everything about Mushrooms and participate in cooking demonstrations, culinary markets, forest mushroom cuisine, wine and beer tasting, and wild mushroom exhibits.
Florence
Florence is a coastal gem adorned with sand dunes and vibrant marine life. A visit to Sea Lion Caves, the country's largest sea cave, would be the highlight of your trip, where you can take in a sea lion statue, whales, sea birds, and bones. You may also embark on dune buggy adventures along the Pacific Ocean beach.
Heceta Head Lighthouse stands proudly atop dramatic cliffs where you can head on the Heceta Lighthouse Trail, spot whales, and enjoy camping on the Washburne campground. Darlingtonia State Natural Site allows you to admire the rare cobra lily or Darlingtonia Californica. The annual Rhododendron Festival showcases colorful blooms and local culture in its Davis Shows carnival, the Coast Radio Classic Car Cruise, and grand floral parade.
Cannon Beach
One of Oregon’s most charming beach towns, Cannon Beach is famed for Haystack Rock, an iconic sea stack that boasts vivid sea stars. The location is also prominent for its accessibility to gaze at Tufted Puffins. The nearby Hug Point State Recreation Site lets you get intimate with the beach, walk the stagecoach trail, and snap the beautiful sitka spruce, ferns, and salal.
You will have a blast while engaging in the annual Sandcastle Contest, an awe-inspiring display of sandy sculptures. The Cannon Beach Gallery hosts local art exhibitions, summer art camps, and Oregon Art Day. Any Cannon Beach getaway would not be complete without visiting the local favorite Bruce's Candy Kitchen, which makes delicious treats like Caramel Corn, Caramel Corn, and Salt Water Taffy.
The Dalles
The Dalles, hugging the Columbia River, is steeped in history where you get to experience pioneer life at the Fort Dalles Museum and admire petroglyphs at Columbia Hills State Park. Outdoor enthusiasts will find solace in the Deschutes River Trail, passing amid lava flows and pine forests, and nearby wineries like Tierra De Lobos Winery, Sunshine Mill, and 15 Mile Winery.
Outdoor enthusiasts find paradise in the diverse offerings of Rock Fort Campsite, from hiking on the Lewis & Clark National Historic Trail to boating in the Columbia River. The annual Northwest Cherry Festival celebrates agricultural heritage. You can also check out the Columbia Gorge Discovery Center, hike to Rowena Crest for panoramic views, and learn about Lewis and Clark's journey.
Whether savoring local wines, partaking in vibrant festivals, or immersing in the richness of nature, Oregon's prettiest towns offer a kaleidoscope of experiences that reflect the state's captivating spirit. From the windswept allure of Hood River, where windsurfing and gourmet delights intertwine, to The Dalles, at the crossroads of history, which invites outdoor exploration, you will find the state's diverse landscapes and vibrant culture, each inviting you to step into a world of beauty, history, and ongoing charm.
