11 Best Downtowns In Oregon
Oregon, “The Beaver State,” is well known for its enchanting landscapes along its Pacific coast and forested interior, but the small-town downtowns that make up the state are something of a wonder in their own right. From the outdoorsy breweries and cafes of Astoria to the historic Victorian architecture of Ashland and riverside views of Hood River, this article will cover the best of the best small downtowns for visitors to explore.
Astoria
The northern Oregon coastal town of Astoria is a treat for a myriad of personalities and vacation goals. Astoria was founded in 1811, making it the oldest city in Oregon. Downtown, visitors can witness aspects of Astoria’s long history in the Columbia River Maritime Museum or Flavel House Museum.
Waterfront Bowline Hotel is an excellent stay option to base on with its own cocktail bar (The Knot Bar), saunas, and unbeatable views of the river. Check out Weird Sisters Freak Boutique for quirky clothing, the Hidden Underground Experience for a unique twist on a traditional shopping mall, and Sea Gypsy Gifts for souvenirs. Plan an upscale dinner at Daphne, a small restaurant with an ever-changing menu of local ingredients and wines.
Ashland
Known for the world-famous Oregon Shakespeare Festival, Victorian architecture, and award-winning art galleries, Ashland is a compelling option for travelers looking for a versatile atmosphere.
Downtown Ashland Springs Hotel is an elegant stay; the building originated in 1925 and has an onsite restaurant, Larks, that serves a variety of local and fusion flavors. In the warmer months, Ashland has an excellent Saturday market with local artisans. Stop in Branson’s Chocolates for some locally made chocolate truffles or Rogue Creamery to watch cheesemakers hard at work before sampling selections of cheddar.
Sisters
Sisters, Oregon, often serves as a base for the great outdoors that surrounds this lovely mountain town, but its downtown is not to be overlooked. Mom-and-pop businesses like the Hen’s Tooth, Stitchin’ Post, and Antler Arts all offer unique, handmade options for gifts and souvenirs.
Stay at the Ski Inn Taphouse and Hotel in the middle of downtown, which has comfortable, modern rooms upstairs, a spread of brews, and classic pub fare on the main level. Hoodoo Ski Resort near Sisters welcomes intermediate and expert snowboarders and skiers in the winter, making Sisters a great base for a ski vacation.
McMinnville
In the heart of Willamette Valley wine country, McMinnville is a coveted destination for wine enthusiasts. Atticus Hotel in downtown McMinnville provides a particular aesthetic with the finest attention to detail fit for any wine connoisseur. The hotel features a unique luxury bunkhouse designed with a best friend’s getaway in mind.
Grab a quick breakfast and coffee at Alchemist’s Jam before taking a tour with Dirty Radish Tour Company to visit boutique wineries within Willamette Valley and downtown McMinnville. The Sage Restaurant is a classic in McMinnville for lunch or dinner, specializing in soups and sandwiches. For shopping and souvenirs, visitors can count on NW Food & Gifts or Left by West for thoughtful gifts and mementos.
Cannon Beach
Scenic walks on the beach and Haystack Rock aren’t all Cannon Beach has to offer. Downtown Cannon Beach is alive with walkable streets, local art in action at House of Orange or Dragon Fire Gallery, and locally owned shops like Love & Hemlock and The Water Witch. Fresh bread and coffee at Sea Level Bakery + Coffee is a great morning starter before exploring nearby Ecola State Park or Arcadia Beach State Recreation Site.
Visitors can grab a sample of whiskey and scotch at MacGregor’s Whiskey Bar before heading to The Driftwood Restaurant & Lounge for a steak dinner. An oceanfront stay at Hallmark Resort & Spa caps off an ideal downtown getaway to Cannon Beach with direct views of Haystack Rock and the Pacific Ocean.
Joseph
Surrounded by alpine lakes, canyons, rivers, and the Wallowa Mountains, Joseph is quite the catch when it comes to an all-around desirable town to visit. Stay at the historic Jennings Hotel on Main Street and walk the short distance up to Ember’s Brewhouse for a beer and oversized pretzel for lunch.
Nearby Wallowa Lake is Joseph's main attraction; visitors can spend their afternoons renting a boat or paddleboard to experience the lake. Mad Mary’s Gift Shop & Soda Fountain is the perfect post-lake stop-in for ice creams, sodas, and souvenirs.
Baker City
Downtown Baker City is a vibrant display of its preserved history and modern design. The award-winning Geiser Grand Hotel is the best choice for visitors to downtown Baker City, with elegant luxury that transcends the decades with its design and original finishes.
Plan a dinner at Latitude Forty-Five Grille and sip locally made brews nearby at North Seven Brewing Co. before catching a movie at the classic 1940s-era Eltrym Theatre. Book lovers will enjoy a stop in Betty’s Books, a cozy shop with staff picks and used options. Download a Baker City Self-Guided Walking & Tasting Tour for a local perspective.
Hood River
Just a short hour away from Portland, Hood River is bursting at the seams with outdoor adventure and an attractive downtown for every traveler. Visitors can enjoy shopping for gifts and souvenirs at quintessential Oregonian storefronts like Spruce Gifts and Provisions and The Ruddy Duck.
Horsefeathers Boutique Hotel features luxury condos in the heart of downtown with comfortable, self-sufficient living areas and views of the Columbia River Gorge. For breakfast and lunch, head to the Scandinavian delight, Broder Ost, for Swedish Hash or Salmon Fishcakes. At dinner, Riverside’s patio is a lovely spot to enjoy Italian fare while enjoying riverfront sunsets.
Yachats
The “Gem of the Oregon Coast”, Yachats truly is a gem worthy status with a downtown to match. Visitors can plan to stay at the Overleaf Lodge & Spa for some unforgettable views of the Pacific coast right from the rooms’ balcony before venturing out for the day to Heceta Head Lighthouse or Cape Perpetua.
Downtown favorite LeRoy’s Blue Whale should be a post-adventure fuel-up with hearty breakfasts or their signature Fish and Chips with clam chowder. Village Gift Gallery and Toad Hall are the best shops to find unique gifts, while Dream Machine Coffee serves a casual pick-me-up with colorful clad coffee mugs and light snacks.
Silverton
Originally a logging town, Silverton is known now as Oregon’s “Garden City,” with 80 acres of plant, wetlands, and water features at The Oregon Garden. In downtown, art enthusiasts enjoy the Lunaria Gallery, a lovely display of fine art paintings, jewelry, and various other forms of creative mediums hand-made in and around Silverton.
Bush Creek Theatre is another favorite spot in Silverton, and it has a myriad of plays throughout the year. There are over 30 murals to wander and admire around downtown Silverton. After a built-up appetite, visitors can grab a tasty, healthy meal at Fin and Fowl Kitchen or a hearty melt at Rustic Melt before finding a comfortable bed at the Silverton Inn & Suites.
Jacksonville
Jacksonville started out as a Gold Rush town, now it’s known as the gateway to the Apple Valley Wine Trail and home to some incredible winemakers and local shops that attract downtown lovers from all over the country. Visitors can stay at the oldest home in Oregon that is still in operation as an inn, The McCully House Inn, and plan for breakfast at GoodBean Coffee.
In the warmer months, the Britt Festival Pavilion comes alive with musical performances. Wine lovers will enjoy the plentiful wine bar offerings at Remotion Wine, South Stage Cellars, and Cowhorn Kitchen and Wine.
Oregon's Unforgettable Small-Town Downtowns
The small-town downtowns that makeup Oregon’s coast and interior are unbeatable destinations to wander. Any traveler looking for an authentic glimpse into Oregon’s small town's unique quirkiness will find it in any one of these towns. Whether visitors are craving a breath of fresh seafoam air or want to be cozied up in a bookshop of a quiet downtown surrounded by lush forest, Oregon’s small-town downtowns will exceed these expectations.
