5 Beautiful Small Towns To Explore In Oregon

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.

# Ashland

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.

# Astoria

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.

# Cannon Beach

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

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.

# Grants Pass

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).