When you think of Oregon, you’ll most likely think of beavers, the popular video game Oregon Trail, and, if you enjoy television, Grimm and The Goonies. But the Beaver State boasts of plentiful attractions outside of Portland that you can sink your teeth into and almost never let go. From dynamic natural wonders, such as Mount Hood and Crater Lake, to picturesque small towns, like Astoria and Cannon Beach, you’ll feel like Lewis and Clark as they settled down in the final leg of their long journey amidst the heart-soothing wildlands and eye-delighting mountain trails of Oregon. So before you travel down your own Oregon trail, consider these top-rated small towns to stop and stay at.
Love The Goonies? Well, Astoria, the “little San Francisco” as it's dubbed, is where the pop-cultural movie was filmed. The town’s maritime relics and Victorian mansions, combined with seafood restaurants and tattoo parlors, continue to offer picture-perfect sceneries of the Pacific Ocean and the American landscape. Bordering both the Pacific Ocean and the Columbia River in northwest Oregon, you can digest the wonders of the land and the sea by taking a stroll down Astoria Riverwalk, visiting the Columbia River Maritime Museum and the Astoria Riverfront Trolley for the seafood and the sights; and taking a peek at breweries in Buoy Beer Company and Fort George. For lodgings, the Astoria Riverwalk Inn provides tranquil views of the Pacific.
Known as the windsurfing capital of the world, Hood River attracts a steadfast stream of trekkers who migrate to the town for its easy access to both Mount Hood and the Columbia River Gorge. The picturesque Mount Hood contains 1,000 miles of trails for hiking, mountain biking, standup paddleboarding, skiing, kiteboarding, windsurfing, kayaking, and other delights for the adventurous. The most popular trails include Timberline Trail, which circumnavigates the whole mountain, and Coopers Spur Trail, which terminates at the highest reachable hiking point.
Beside the national landmark is the Columbia River Gorge, a dwelling of many of Oregon's best waterfalls. Strewn along the silvery rushes are hiking trails, campgrounds, and places where high winds are so strong you can windsurf on them. And if you ever get exhausted from the trekking, the fun, and nature’s artistry, take a nap in Hampton Inn and Suites Hood River or Columbia Gorge Hotel and Spa.
Jacksonville, located 5 miles west of Medford and cradled in the Siskiyou Mountains, is both an idyllic small town and a National Historic Landmark. Gold deposits from the 1850s drew prosperity and settlers before Oregon officially became a state. These days, Jacksonville is better known for its yearly Britt Music & Arts Festival, which attracts a plethora of music lovers from across the world with performances ranging from reggae to classical. Come summertime, the Jacksonville Trolley offers a 45-minute tour of the region's unique history and architecture, allowing modern visitors to glimpse the old-school Americana charm and the epicurean joys of the Gold Rush.
Its shopping centers are also an ideal blend of the cowboy era and modern sensibilities, with downtown boasting innumerable one-of-a-kind souvenir shops, antique stores, boutiques, bookstores, luxury hotels, and award-winning restaurants. When you’re not touring the past or enjoying the hip and awesome music in the area, you can always stay in the Wine Country Inn, Kubli Haus, Magnolia Hotel, and The Jacksonville Inn.
Though home to fewer than 2,000 residents, the small town of Cannon Beach throngs with hundreds of thousands of visitors annually. Cannon Beach’s long stretch of crystal-bright sand and the spear-sharp, 235-foot-tall Haystack Rock looming above the tides create a mystical, mesmerizing coastline with photo-worthy seascapes and views that will leave you astounded. No small wonder this town, so named after a naval cannon that swept up after a shipwreck, has been labeled one of the 100 most beautiful places by National Geographic in 2013.
Its surrounding geography is equally favored, for to the north of Cannon Beach, trails in Ecola State Park offer sweeping views of the ocean, while Arcadia Beach to the south contains tide pools and a picnic area to relax in. Only 90 minutes from Portland, you can book a stay in The Wayside Inn, Beachcomber Vacation Home, or Argonauta Inn for a perfect beach getaway where you can swim, sunbathe, and beach comb whilst surrounded by beautiful scenery.
Baker City is known as "eastern Oregon's base camp" because of its historical ties to the renowned Oregon Trail. The town was a prosperous trading and resting hub between Salt Lake City and Portland for innumerable travelers and migrants since its establishment in 1874, a route that the original Oregon trail passed by. It continued to provide exemplary services through the Geiser Grand Hotel, a four-star hostel opened in 1889 with a long history of welcoming guests with luxurious accommodations. Places like the Baker Heritage Museum or the Eastern Oregon Museum also present historical windows to Oregon’s past. The National Historic Oregon Trail Interpretive Center also provides an informative day trip to learn more about Oregon’s massive human migrations.
The "Little Switzerland of America" is a title that the adorable town of Joseph exemplifies. The town, embraced by the Wallowa Mountains in the south and west and hovers beside the foreboding Hells Canyon in the north and east, honors Chief Joseph of the Nez Perce tribe, from whom the town derives its name, by hosting an annual Tamkaliks celebration that includes a friendship feast awaited eagerly by residents and Nez Perce descendants. If you miss the celebration, you can take a trip to Wallowa Lake—renowned for its trophy-sized fish—or explore the Eagle Cap Wilderness hikes for more adventures.
On sidewalks flanked by art galleries and seven life-size bronze sculptures, you'll find gear outfitters, the Wallowa County Museum, and a seasonal Wallowa County Farmers' Market. For places to stay, look no closer than the Bronze Antler Bed & Breakfast, Eagle Cap Chalets, Flying Arrow Resort, or Trouthaven Resort.
The wave-carved inlet known as Devils Churn and the nearby Thor's Well, a swirling hole in the basalt rocks, gulps the Pacific Ocean in the south. To the west, the rugged shores; east, the sprawling Siuslaw National Forest. And in the middle of these intense and natural landscapes is the scenic town of Yachats. The town’s name (pronounced yah-hots) comes from the Chinook word for "dark water at the foot of the mountain,” and visitors can take either the Ya’Xiak (yah' khik) Trail or Amanda's Trail—part of the much longer Oregon Coast Trail—to witness scenic views of the meandering, forested landscape. Amanda’s Trail, specifically, is the entranceway to Cape Perpetua, the highest point on the Oregon Coast, a breathtaking vista that has been labeled one of the top-rated attractions on the Oregon Coast. Book a room or more in opulent lodgings like the Dublin House Motel, Deane's Oceanfront Lodge, Ocean Cove Inn, and Silver Surf Motel.
Silverton is located 15 miles northeast of Salem and 45 miles south of Portland. These days, the cute town is affectionately known as Oregon's Garden City, and while many perennial charms support this moniker, it is the Oregon Garden that best expresses Silverton's horticultural appeal. Over 80 acres of beautiful botanic park, comprised of several specialty plots like a Children's Garden and a Pet-Friendly Garden, often hosting several events throughout the year, such as the Arts in the Garden. Nearby, Silver Falls State Park, home to the nationally recognized "Trail of Ten Falls," is a popular attraction. In town are resting places like the Oregon Garden Resort, the Silverton Inn and Suites, Edward Adams House B&B, and the Silver Spur RV Park.
Three volcanic peaks—the Sisters—loom titanically to the west of this pretty small town, resplendent with vibrant modern artworks and 1880s facades. Sandwiched between the Cascade Mountains in central Oregon and the state’s high-desert region, Sisters thrives with a smorgasbord of diverse biomes, from the towering alpine vistas of the Three Sisters to the ponderosa pine forests of Deschutes National Forest and 650 acres of arid deserts that constitutes the Smith Rock State Park. Adventure awaits on country-spanning trails like the Pacific Crest Trail, and you can take a breather in Best Western Ponderosa Lodge, the Black Butte Ranch Vacation Rentals, Fish Inn Bike Inn, FivePine Lodge and Cottages, and Long Hollow Ranch.
Theater-lovers rejoice! From February through November, Ashland hosts the time-honored Oregon Shakespeare Festival, where artists, creators, tourists, and locals partake in unique adaptations or originals of the Bard’s transcendental plays, be they audience or actors. Aside from these theatrical displays, you can peruse the Ashland Artworks Gallery or the Schneider Museum of Art, where some of the best regional artists and their works are prominently featured.
Ashland is situated near Bear Creek, in the southern reaches of the Rogue River Valley, and at the base of the Siskiyou Mountains, just southeast of Medford. Due to its proximity to natural landmarks, you can venture out and marvel at the town's ties to the land. Traipse about in Lithia Park or on the slopes of Mount Ashland whilst contemplating the Shakespearean observations, ruminating on the follies of man and the majesties of American wildlife. But remember to settle in travel-friendly hotels like Swank & House, The Winchester Inn, StayAshland, or The Bard’s Inn Hotel.
The area around The Dalles is known to have been a trading center for Native Americans as long as 10,000 years ago, thus making the town one of the oldest inhabited places in North America. Visitors can learn about The Dalles’ unique history in the Columbia Gorge Discovery Center and Museum, where several interactive exhibits explain the visit from the Lewis and Clark Expedition in 1805. You can also explore the Fort Dalles historic site, a replica of the 1850s US Army Outpost that showcases the town’s pioneering heritage, or the Maryhill Museum of Art, which offers an excellent view of the Columbia River Gorge.
Outside of history, this vibrant region of the Columbia River Gorge provides plenty of hiking adventures 20 miles east of Hood River and near the Deschutes River. And because The Dalles is the terminus of the old Oregon Trail, consider settling down here after your Oregon trail is finished at the Fairfield Inn and Suites, The Dalles, Cousins Country Inn, Comfort Inn Columbia Gorge, or Celilo Inn.
Your travels along Oregon's many trails are just beginning. The many attractions each small town has to offer are nibbles and bites of more enticing natural and cultural wonders from Oregon's countryside. From movie-worthy towns like Astoria to nature-appealing landscapes like Yachats, Oregon still has many surprises awaiting the curious, the brave, and the adventurous. So sink your big teeth deeper into the Beaver State and start your own expedition where Lewis and Clark ended theirs.