Oregon is probably best known for its largest city, Portland, but the state has far more mid-sized and small towns than it does big cities. These small towns are great places to get outdoors, enjoy some delicious Northwest cuisine, delve into local history, go wine tasting, or even spend time on the Oregon coast.
If you like your small towns artsy, then Ashland is the place for you. Probably best known for the Oregon Shakespeare Festival, Ashland is home to a number of other arts institutions and festivals, including the Ashland Independent Film Festival, Ashland New Plays Festival, and the Schneider Museum of Art. But Ashland isn't just a cultural hub. Close to both the Siskiyou and Cascade mountain ranges, you’ll find plenty of outdoor adventure near Ashland. The Mount Ashland Ski Area is also nearby if you’re visiting in the colder months. For everyday outdoor fun, a visit to Lithia Park is always a great idea. Located right in town, this 100-acre park has everything from trails, both rough and paved, to an amphitheater.
Named for John Jacob Astor, Astoria is a quaint town located where the Columbia River meets the Pacific Ocean. The houses lining the hilly streets leading down to the water are incredibly charming, and there’s even a trolley that goes straight through the heart of town. Wandering the streets and dipping into shops and restaurants is a fine way to spend an afternoon.
Astoria also gets a fair number of "Goonies" fans stopping through, and you can see a number of film locations in town (but keep your distance from the actual "Goonies" house as it’s a private residence). Other highlights include the Astoria Column (which you can climb to get a commanding view of the surrounding area) the Columbia River Maritime Museum, and the beautiful Captain George Flavel House Museum (which also made an appearance in "Goonies"). If you like looking at wildlife, head to the dock behind the Comfort Suites to catch sight of some sea lions.
Cannon Beach is one of many small towns along the Oregon Coast, but it’s one with ample small-town appeal and not just beach town appeal. The heart of Cannon Beach is home to several art galleries, a brewery or two, a distillery, and several restaurants. There’s no finer evening than hopping between bites to eat and exploring the galleries and shops (don’t miss the requisite beach sweet shops). Cap your evening off with a show at the Coaster Theatre Playhouse, a cooking class, or stop by Icefire Glassworks to watch a live glassblowing session. Of course, this is a beach town so getting out on the beach is a must. The towering Haystack Rock (a huge, 200-foot-tall sea stack) is just offshore, impossible to miss and covered with seabirds (bring your binoculars!).
The Dalles puts you in close proximity to gorgeous scenery and plenty of outdoorsy adventure. With Hood River just down I-84, you can zip over that way for some world-class windsurfing, but since The Dalles is right on the Columbia River you can go paddling, kayaking, fishing without leaving town. You can also test your mettle on some of the hiking and mountain biking trails.
If you'd like to learn a little something, stop by the Fort Dalles Museum to learn about the town and region’s history, or visit the Dalles Dam Visitor Center where you can learn about the dam, view some fish, and enjoy some kids activities. The Dalles is also known for its food and drink. Look for amazing local cherries in the summer, and don’t miss stopping by a local winery!
Grants Pass is Oregon’s whitewater rafting capital. Go rafting with a tour and enjoy the spectacular scenery of the river up close and personal, or if you’re not much for getting out on the water, enjoy the beauty of the river by hiking on trails in the Rogue River Canyon (about a half-hour out of Grants Pass).
Once you're done in nature, you can tour the historic buildings of downtown Grants Pass. The area is a National Historic District and you can take a self-guided walking tour if you stop by the Welcome Center for a map. Downtown is also a fine place to shop and dine. There are a number of wineries in the nearby Applegate Valley so expect some local wine to greet you at the restaurants.
Hood River is a little town with a lot to offer including food, drink, and outdoorsy pursuits. The wind whipping down the Columbia River is world-class and perfect for windsurfing (Hood River is called the Windsurfing Capital of the World for a reason). If you aren’t up for whipping your way over (and sometimes above) the water, other outdoor fun in the area includes fishing, boating, hiking, mountain biking, and otherwise enjoying the trails.
Hood River is also known for an abundance of fresh, local produce. If you want to experience the area's agricultural side, drive the Fruit Loop, which takes you past several farms and farm stands. If you'd rather have the local produce prepared for you, Solstice Woodfire Café & Bar right on the river is a good bet for both food and drink.
Joseph is an outdoor lover’s dream. Perched right on the edge of Wallowa Lake and surrounded by the picturesque Wallowa mountain range, expect some top-notch scenery around every corner. Visit Wallowa Lake State Park for some stellar fishing, kayaking, paddling, and motorboating. But also don’t miss the shops and restaurants in town, which include all the best things in life like bakeries, chocolate shops, and coffee shops.
McMinnville is an adorable town with a quaint downtown complete with tree-lined streets and plenty of shops to explore. Along with the usual nearby trails for hiking and cycling that most Northwest cities and towns have, McMinnville has a few unique things to see.
The Evergreen Aviation and Space Museum, which is home to the Spruce Goose, the world’s largest propeller-driven (and completely wooden!) aircraft. It was built by Howard Hughes for WWII, but was never used because it wasn't finished in time. McMinnville is also known for some UFO photos published in a local paper in 1950 and hosts an annual UFO Festival to that honor. Yet another fun attraction worth checking out, especially if you’re visiting with kids, is the Galen McBee Airport Park, which gets its name from its proximity to the town's small airport and features trails highlighted by some concrete sculptures, including a very adorable mushroom house that makes for great photos.