8 Cutest Small Towns In Oregon To Visit In 2024

In the Pacific Northwest region of the US, Oregon is renowned for its lush green forests, quirky brewery-boasting towns, majestic mountains and rivers, and a breathtaking coastline that kisses the borderlines of Washington and California. While more populous cities like Portland and Bend are among the state’s go-to destinations, there are plenty of hidden gems tucked into its tapestry. From quiet coastal villages like Astoria to quaint western-themed towns like Sisters, these off-the-beaten-path oases are charming locales for your next Oregon adventure.

Sisters

Named after the picturesque Three Sisters Mountain Range, Sisters sits quietly in Deschutes County, about 25 miles west of Bend. With walkable streets adorned with 1800s-inspired architecture, the quaint western-themed town is a popular Central Oregon tourist spot, especially during the summer months when annual events like Sisters Outdoor Quilt Show, and the Sisters Rodeo are in full swing. You don’t have to be a cowboy to lasso up some Old West charm. The Sisters Saloon & Ranch Grill serves up homestyle grub in a historic 1912 building. The town’s lone grocery store, Rays, is housed in a general store-style building. Even the local movie theater, Sisters Movie House, screens films in a barn-shaped locale. Sitting at the entryway of the gorgeous Three Sisters Wilderness, there is also a plethora of outdoor adventures, like hiking, camping, and waterfall-chasing, all within reach. From small-town charm to natural wonders, Sisters is a true gem.

Redmond

The High Desert town of Redmond rests about 15 miles north of bustling Bend. Packed with local breweries, like Wild Ride Brewing Co. and Cascade Lakes, food truck pods, and eclectic brick-and-mortar eateries, there are plenty of options to wet your whistle or fill your gullet. A small, walkable downtown boasts an array of boutiques and antique shops amidst a vibrant arts community. During the summer, the town hosts the Deschutes County Fair, which features free concerts at the price of admission and a lively rodeo. On the outskirts of town, the Eagle Crest Resort offers vacation rental homes, pools and spas, and golf courses with the majestic backdrop of the Cascade Mountain Range. Nearby Smith Rock State Park is a sprawling outdoor playground for hikers, bikers, and four-legged friends.

Hood River

Tucked into the Columbia River Gorge an hour outside of Portland, Hood River is a treasure of the Pacific Northwest. With a quaint downtown full of craft breweries, wineries, and farm-to-table eateries, there’s plenty to sip and nibble on while taking in the picturesque views of Mt. Hood. Known as the “Windsurfing Capital of the World,” water sport enthusiasts can surf the windy Columbia Gorge, while land adventurers will find a bounty of scenic hiking trails nearby. After a day of exploring all the wonders Mt. Hood has to offer, visitors can check in to the historic Hood River Hotel. Dating back to 1912, the hotel is adorned with period-style furnishings, a vintage cocktail lounge, and a restaurant with Scandinavian fare.

Cottage Grove

Just south of Eugene, Cottage Grove boasts small-town charm with a big heart. Artfully decorated with vibrant murals, its historic downtown district is densely packed with locally-owned restaurants, antique shops, bookstores, and boutiques. Take a drive through the forest-veiled countryside and discover the town’s historic bridges. Hailed as the Covered Bridge Capital of Oregon, Cottage Grove is home to six covered bridges, including the only remaining railroad bridge west of the Mississippi, and a filming location for the coming-of-age classic Stand By Me. While there are several hotels in town, you can also rent your very own cottage in the woods for a peaceful getaway in the wild.

Ashland

At the base of Oregon, near the border of California, rests the art-imbued town of Ashland. Recognized in the top ten of “The 100 Best Small Art Towns in America,” it’s home to a vibrant theater scene and host to the world-renowned Oregon Shakespeare Festival, which runs from May through October. Outside of performance arts, Ashland visitors can enjoy the beauty of the outdoors by hiking amidst the Cascade-Siskiyou National Monument or taking a scenic drive two hours north to Crater Lake. For those who wish to get outside closer to town, Ashland’s Lithia Park downtown is lush with greenery, a Japanese garden, and a duck pond. Literary lovers may be interested to know that Russian author Vladimir Nabakov completed his famous novel Lolita while living in Ashland. While his former residence was lost in a fire, there is a commemorative plaque in its place. Full of art and history, Ashland is a perfect destination for a small-town getaway.

Mcminnville

Surrounded by rolling vineyard hills and picturesque Pacific Northwest landscapes, McMinnville sits in the heart of Oregon wine country. With 250 Willamette Valley wineries, like The Erie Vineyards and Youngberg Hill, all within 20 miles of town, the area is ripe with options for local tastings. Stroll the historic downtown district, whose twinkle light-adorned streets are lined with boutiques, vintage shops, and eclectic eateries. Those staying in town have an array of charming bungalows, cottages, and hotels to choose from. The historic Mcmenamins Hotel Oregon is a favorite amongst travelers, featuring rooftop and cellar bars and a restaurant serving classic pub fare. For a unique stay on the outskirts of town, the Vintages Trailer Resort rents out refurbished retro trailers in an idyllic setting where luxury meets the great outdoors.

Gearhart

A quiet, lesser-known coastal town in Oregon, Gearhart sits three miles north of the tourist-packed Seaside. Its wide streets with no traffic lights give a taste of a slower-paced lifestyle, while a 20-mile stretch of pristine, unpopulated beaches offers a peaceful oceanside retreat. Home to the oldest golf course in the Pacific Northwest, the 18-hole Gearhart Golf Links shares its property with the historic McMenamins Gearhart Hotel, where guests can unwind in the cozy Sand Trap Pub after a day on the greens. With bustling coastal towns like Cannon Beach and Astoria nearby, Gearhart is a secluded gem on the stunning Oregon Coast.

Astoria

Cradled by forests, rivers, and ocean beaches, Astoria has all the wonders of the Pacific Northwest in its backyard. Revered as Oregon’s “Little San Francisco,” the fable-like port village features Victorian mansions, dockside eateries and breweries, and a bustling downtown that merges hip with historic. There’s plenty of history packed into the small town, which is documented in an array of local museums, from the Oregon Film Museum to the Columbia River Maritime Museum. As haunting as it is beautiful, the seaside haven is a must-visit on the northern Oregon Coast.

The Takeaway

Whether you’re a nature enthusiast or the indoor artistic type, Oregon has something to offer everyone. Amidst its stunning scenic landscapes and vibrant metropolises, the charming small towns are the heart and soul of the breathtaking Beaver State. From historic locales brimming with arts and culture scenes like Ashland to secluded forest-shrouded villages boasting idyllic covered bridges like Cottage Grove, there are endless gems to uncover and explore in Oregon.