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 little locales that really exemplify peak Oregon living: beautiful scenery, world-class recreation, small-town vibes, amazing restaurants, and some of the best shopping in Oregon, too. 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 that are just perfect for a weekend escape — and some of the best small town shopping in Oregon, too!

1. Jacksonville
Jacksonville, OR 97530, USA
Jacksonville Oregon/Facebook
Not only is Jacksonville a charming little locale, it's also one of the coolest towns in the PNW! Why you ask? Well, it turns out Jacksonville is home to an incredible annual music festival that draws some of the biggest bands and artists in the industry, too!
2. Ashland
Ashland, OR 97520, USA
Jeff Hitchcock/Flickr
Ashland is known for its thriving arts scene and free-spirited community, and it's truly a delightful place to visit. 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!
3. Condon
Condon, OR 97823, USA
Condon Chamber of Commerce/Facebook
Located about 2.5 hours east of Portland, the tiny town of Condon has a rich history that spans more than 125 years! Its charming Main Street is full of historic buildings that have recently been restored, many of which are also listed on the National Register of Historic Places. If you're into history, a visit to Condon is a must; you can take the experience to the next level by booking a night at Hotel Condon, a landmark hotel that's over a century old!
4. Sisters
Sisters, OR 97759, USA
m01229/Flickr
With a population of just 2,000, Sisters is the kind of small town where everyone knows your name. This Oregon town is big on tradition, with annual events like the Outdoor Quilt Show, Sisters Folk Fest, and Sisters Rodeo attracting folks from all over the state! When in Sisters, definitely stay at FivePine Lodge, an award-winning, woodsy lodge where you can book a cabin or suite year-round. Come and experience peak Oregon small-town life in Sisters!

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5. Yachats
Yachats, OR, USA
Visit Yachats Oregon Coast/Facebook
Yachats is a treasure of a town, offering Oregonians a perfect slice of small-town coastal living. No matter where you are in Yachats, you're sure to have spectacular shoreline views. Take a little coastal retreat in this charming little locale; while you're there, we highly recommend staying at the Drift Inn Hotel and Restaurant, a beloved Yachats establishment.
6. Cottage Grove
Cottage Grove, OR 97424, USA
Bruce Fingerhood/Flickr
You'll find the quaint town of Cottage Grove just 20 miles south of Eugene. The town is home to around 10,000 people, which means it's large enough to have plenty of big-city amenities but still small enough that it still has that small-town spirit. There's a lot to see and do in Cottage Grove, from browsing its bustling downtown to visiting one of the town's six historic covered bridges. Cottage Grove is also home to Saginaw Vineyard, which is a breathtakingly beautiful Oregon winery. Come to Cottage Grove for a weekend of wandering... and wine!
7. Hood River
Hood River, OR 97031, USA
Sam Beebe/Wikipedia
Hood River is one of the most stunningly beautiful places in the state, nestled in the sublime shadow of majestic Mt. Hood. This town of just 1,000 residents is known for its incredible outdoor recreation, offering everything from hiking and biking to kayaking and wind surfing. In terms of best small town shopping in Oregon, Hood River has a stretch of shops that's absolutely delightful for the whole family, even boasting an epic treehouse for kids to climb around on! To best enjoy Hood River's epic panoramas, definitely book a night or two at Columbia Cliff Villas, a charming hotel that's situated on a dramatic bluff 200 feet above the mighty Columbia River!
8. Florence
Florence, OR 97439, USA
Florence Chamber of Commerce
It really doesn't get any more postcard-perfect than Florence. This sleepy little beach town has amazing waterfront restaurants, charming shops, and some of the best shorelines in all of Oregon! When you visit, be sure to stay at the Lighthouse Inn, a 75-year-old hotel located in the heart of the town's historic downtown district.

Tell us: what are your favorite small towns in the Beaver State? Your picks for the best small town shopping in Oregon? Do you live in any of these places? Share your thoughts in the comments below! And if you’d like to nominate your own small town to be featured in an upcoming Only In Oregon article, please nominate it and tell us why it’s such a special place!

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More to Explore

best small town shopping in Oregon

Sarah M. | September 12, 2022

What are some other little locales known for amazing small town shopping in Oregon?

Cannon Beach is arguably the most well-known spot on the Oregon Coast, famed for its stunning shores and iconic rock formations. But Cannon Beach isn’t just one of the Beaver State's most beautiful beaches, it’s also an idyllic seaside town that’s home to some of the most charming little shops and local businesses in the PNW. We're talking about a coastal locale that's straight out of a Hallmark movie, with weather-worn buildings housing some of the most amazing little restaurants, retailers, and accommodations. For those with a sweet tooth, Bruce's Candy Kitchen is a perennial favorite, with its pink-and-white striped shop welcoming folks since 1963, while Cannon Beach Hardware and Public House is a quirky little spot that's got a bit of everything: hardware, wines, and even pub grub. And when looking for accommodations in Cannon Beach, the Stephanie Inn is known for having the best views in town!

Another small town in Oregon with a superlative shopping scene is Bend. While not as small as some of the others on this list, Bend has a vibrant downtown district that offers everything from waterfront dining and amazing parks to adorable bookstores and locally-owned shops! Oh, and did we mention that Bend is also home to the last remaining Blockbuster in the entire world?!?

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