15 Charming Small Towns in Oregon

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From California to Connecticut, small towns are having a major moment. In our humble opinion, it’s high time these tiny treasures got the recognition they deserve. This brings us to the great state of Oregon—a place known for its pioneering past, unique quirks and natural beauty. We’re talkin’ flowing rivers, snow-capped peaks, empty beaches, verdant valleys and rolling vineyards.

Keen to discover the true spirit (and scenery) of the Beaver State? Scroll on for 15 of the most charming small towns in Oregon.


charming small towns in oregon hood river
Anna Gorin/Getty Images

1. Hood River, Or

When you hear “windsurfing capital of the world,” what springs to mind? Probably some breezy destination in California or the Caribbean. Well, it’s actually Hood River! If windsurfing doesn’t float your boat (sorry, we couldn’t resist), rest assured that Mount Hood provides countless opportunities for hiking, biking and skiing. There’s also fishing and kayaking on the Columbia River.

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charming small towns in oregon sumpter
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2. Sumpter, Or

The state with the most ghost towns? Oregon! And Sumpter is perhaps the most intriguing of the bunch. Platted in 1898, this former gold mining hub showcases many reminders of the past—abandoned churches, saloons, newspapers, and an opera house. True to its Wild West roots, adventure awaits around every corner. As the gateway to the Blue Mountains, Sumpter also puts travelers in proximity to rugged trails.

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charming small towns in oregon cannon beach
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3. Cannon Beach, Or

One of the most photographed towns in the whole of the Pacific Northwest, Cannon Beach boasts scenery so stunning it’s hard to describe in words. (But we’ll give it a shot.) Expect a craggy coastline punctuated by the morning mist, secluded coves, tidal pools and lighthouses. You don’t have to be a shutterbug to appreciate the art galleries, boutiques, and distilleries.

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charming small towns in oregon yachats
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4. Yachats, Or

Yachats (pronounced Yah-hots) comes from the Chinook word Yahut, which means “dark water at the foot of the mountain"—an accurate way to describe this coastal enclave that’s wedged in between the splendor of Devil's Churn and Thor's Well. The town of Yachats itself has numerous galleries displaying Native American works of art, gift shops and seafood restaurants. Nearby Cape Perpetua is a bucket-list hike.

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charming small towns in oregon mcminnville
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5. Mcminnville, Or

Nestled in the heart of Willamette Valley, McMinnville is dotted with coffee shops, farm-to-table restaurants and tasting rooms. Of course, you’ll also want to venture beyond the main drag to one of the many family-run wineries that produce some of the best Pinot noir outside of Burgundy. For a hit of cosmopolitan panache, check out the ultra-chic Atticus Hotel.

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charming small towns in oregonjoseph
John Elk/Getty Images

6. Joseph, Or

Where can you see ranch hands wearing wide-brimmed hats, accomplished trekkers just back from conquering a snow-capped peak, artists in paint-splattered overalls and wide-eyed tourists strolling the same cobblestone sidewalks? Joseph. This small town in northeast Oregon turns on the charm in a big way. It’s rugged, down-to-earth, hip and artsy all at the same time. There’s just no place quite like it.

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charming small towns in oregon gearhart

7. Gearhart, Or

Far away from the hustle and bustle of big-city living, the quaint coastal town of Gearhart doesn't even have traffic lights. What you will find are antique shops, local spots to buy home goods, an art gallery as well as James Beard-approved restaurants that serve Pacific Northwest seafood staples like local Dungeness crab, salmon, oysters and mussels.

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charming small towns in oregon astoria Images

8. Astoria, Or

Bet you didn’t know that Astoria holds the title of oldest settlement west of the Rockies. Victorian-era homes and museums recall the history of this centuries-old fishing village, while innovative breweries add a modern touch to the mix. Since Astoria is perched on the Columbia River, just a few miles from the Pacific Ocean, visitors can take advantage of everything from stand-up paddleboarding to coho fishing.

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charming small towns in oregon baker city
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9. Baker City, Or

Don’t let the name confuse you, Baker City is a small town that's steeped in history. An old-school trading post set along the Oregon Train (yes, the real thing that inspired the popular computer game), this eastern Oregon gem lures tourists with its Victorian-era buildings, indie shops and museums. No trip to Baker City would be complete without a visit to the National Historic Oregon Trail Interpretive Center.

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charming small towns in oregon florence
Francesco Vaninetti Photo/Getty Images

10. Florence, Or

Situated at the mouth of the Siuslaw River Florence has more scenic sights than residents (OK, not literally, but you get the picture). So it’s no wonder this coastal idyll lures nature lovers and adventurers. On the mile-long list of outdoor attractions? The Sea Lion Cave, expansive sand dunes and the hiking trails leading to Heceta Head Lighthouse. With any luck, you might even spy gray whales.

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charming small towns in oregon the dalles
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11. The Dalles, Or

The eastern gateway to the Columbia River Gorge National Scenic Area, The Dalles is one of those rare places that impresses on every level. It’s an epic home base for hiking, biking and fishing. The past is very much alive thanks to the many museums and murals that cover the landmark downtown buildings while wineries give visitors a chance to savor local sips.

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charming small towns in oregon jacksonville
John Elk/Getty Images

12. Jacksonville, Or

Placer gold was found in Jackson Creek back in the 1850s. And so begins the gilded legacy of Jacksonville. Today, this 19th-century mining town flaunts more than 100 buildings on the National Register of Historic Places, including enchanting Victorian-era homes. Tasting rooms, boutiques, homestyle restaurants and live music number among the enticing modern attributes.

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charming small towns in oregon silverton
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13. Silverton, Or

Established in 1854, Silverton literally popped up, err was planned, around a large white oak tree. This imposing natural landmark has long served as a meeting point for Native Americans and, more recently, tourists looking to snap photos. Adding to the list of must-see attractions? A sprawling 80-acre botanical garden with gorgeous blooms and Silver Falls State Park.

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charming small towns in oregon sisters
Amy Meredith/Flickr

14. Sisters, Or

It’s downright impossible not to fall for Sisters. Framed by a trio of peaks to the west, this mountain town will steal your heart with its fresh alpine air, laid-back pace and creative spirit. Other reasons we’re sweet on Sisters include excellent biking, hiking and skiing. Did we mention it’s home to America's first beer spa? Name a more only-in-Oregon activity. Seriously.

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charming small towns in oregon brownsville

15. Brownsville, Or

With fewer than 2,000 residents, Brownsville definitely falls into the category of a small town. Population size aside, this quaint community in the foothills of the Cascade Mountains—which you might recognize as Castle Rock from the 1986 flick Stand by Me—feels frozen in time. Strolling the streets of downtown, it could easily be 1921 or 2021. Don’t forget to visit The Moyer House.

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Freelance PureWow Editor

Lindsay Cohn is a travel writer and serial trip planner who has visited 46 countries across six continents (and counting). When not globetrotting, she’s most likely either doing...