Here Are The 21 Coolest Small Towns In Oregon You’ve Probably Never Heard Of

From gorgeous coastal villages to close-knit farming communities, there are charming small towns in Oregon full of amazing history, beautiful scenery, vibrant downtowns, and great people. Today we’re shining the spotlight on some of the absolute coolest small towns in Oregon, some of which are total under-the-radar hidden gems!

What’s on your list of the coolest small towns in Oregon? Did we miss any of your favorite little locales? Share them in the comments below, or nominate your favorite town for a chance to be featured in an upcoming article!

Address: Coos Bay, OR, USA
Address: Silverton, OR 97381, USA
Address: Talent, OR 97540, USA
Address: Brownsville, OR 97327, USA
Address: Bandon, OR 97411, USA
Address: Drain, OR, USA
Address: Florence, OR 97439, USA
Address: Brookings, OR 97415, USA
Address: Coquille, OR 97423, USA
Address: Carlton, OR 97111, USA
Address: Aurora, OR 97002, USA
Address: Vernonia, OR 97064, USA
Address: Baker City, OR 97814, USA
Address: Wheeler, OR, USA
Address: Joseph, OR 97846, USA
Address: Riddle, OR 97469, USA
Address: Paisley, OR 97636, USA
Address: Gold Beach, OR 97444, USA
Address: Astoria, OR 97103, USA
Address: Sisters, OR 97759, USA
Address: Oakland, OR 97462, USA
The OIYS Visitor Center

Coolest Small Towns in Oregon

August 30, 2021

What’s the coolest small town in Oregon?

Well, ‘cool’ is relative, but we think everyone can agree that Jacksonville is the coolest small town in Oregon! Nestled in the heart of Southern Oregon’s Wine Country, Jacksonville is a small town that’s big on charm — and coolness. For starters, Jacksonville is home to an epic music festival, which is peak *cool* vibes. It’s also full of history; its downtown Historic District is actually listed on the National Registrar of Historic Places, in fact! And Jacksonville is also peak Beaver State beauty, as its location in Wine Country means lots of lovely scenery and wonderful opportunities for outdoor recreation… and wine tasting!

What’s the quirkiest town in Oregon?

In a state that’s known for keeping it weird, there are numerous small towns in Oregon full of quirky charm. We’re big fans of Ashland, a place that’s well-known for its thriving arts scene and free-spirited community. The centerpiece of the town is the Oregon Shakespeare Festival. Founded in 1935, this live theatre venue is straight out of the 1600s, complete with the troupe’s iconic outdoor Allen Elizabethan Theatre, which opens in early June and runs through mid-October. We recommend checking the company’s schedule and planning a little weekend getaway full of theatre and small-town charm! 

What are some of the best small towns in Oregon to visit?

Oregon’s larger cities may get most of the spotlight, but The Beaver State’s small towns are nothing short of wonderful. All across the state, there are some downright delightful small towns that really exemplify peak Oregon living. Whether it’s a charming coastal city, small mountain municipality, wine country province, or a little locale in the state’s rugged outback, Oregon has some of the most winsome small towns in the PNW. Here are eight small towns in Oregon that are just perfect for a weekend escape — we challenge you to visit (and be charmed by) them all!

Address: Coos Bay, OR, USA
Address: Silverton, OR 97381, USA
Address: Talent, OR 97540, USA
Address: Brownsville, OR 97327, USA
Address: Bandon, OR 97411, USA
Address: Drain, OR, USA
Address: Florence, OR 97439, USA
Address: Brookings, OR 97415, USA
Address: Coquille, OR 97423, USA
Address: Carlton, OR 97111, USA
Address: Aurora, OR 97002, USA
Address: Vernonia, OR 97064, USA
Address: Baker City, OR 97814, USA
Address: Wheeler, OR, USA
Address: Joseph, OR 97846, USA
Address: Riddle, OR 97469, USA
Address: Paisley, OR 97636, USA
Address: Gold Beach, OR 97444, USA
Address: Astoria, OR 97103, USA
Address: Sisters, OR 97759, USA
Address: Oakland, OR 97462, USA