Looking out over the coast in Brookings, Oregon.

11 of the Most Quaint Small Towns in Oregon

Have you ever wanted to go back in time and experience the marvels of simple, small-town living? These towns are for the dreamers, the kind easily inspired by both the aesthetic exquisiteness of nature and the authentic charm of small-town values.

The state of Oregon is known for its intellect and progressive politics, such as public access to health care and recreational and medical marijuana. This is all set in the backdrop of Crater Lake, the deepest Lake in the country, the geological wonder of Haystack Rock, and the sublime Columbia River Gorge. Combine that with an intriguing history within towns bursting with friendly people, art galleries, unique boutiques, and adventurous activities, and a quaint experience awaits.

Hood River

Hood River in Oregon with Mount Hood.
Hood River in Oregon with Mount Hood.

This town looks like it was directly lifted from a postcard. Hood River is at the crossroads of the Columbia River Gorge and the Cascade Range, cresting with a sublime view of the mountaintop and sparkling crystal waters. This town is the perfect choice for adrenaline junkies and outdoor enthusiasts, with options for hiking, mountain biking, and even windsurfing coming out of the wazoo. Try the Indian Creek Trail, which moves through the heart of the town, or Post Canyon Seven Streams Tail, which has bumpy terrain made specifically for mountain bikers. Easier hikes for the average traveler are Mirror Lake Trail and Horsetail Falls to the Columbia River Gorge, with the reward of a pretty natural waterfall at the end.

Visitors can gather a plentiful bounty at Hood River U-Pick Organic, a family-run orchard that produces organic honey crisp and gala apples, along with cherries in the summer. Wine country is vast in Hood River, including Stolz Winery, which overlooks the Columbia River Gorge or Cerulean. E-bikes are available on Front Street of the town, as are Mountain Bikes at Hood River Mountain Bike Adventures. Travelers can top off their trip with a visit to the History Museum of Hood River County to engage with the town’s heritage.


Street view in Ashland, Oregon.
Downtown Ashland, Oregon. Image credit Nature's Charm via Shutterstock.com

Ashland is a cultural hub of the state of Oregon, nestled sweetly at the base of the Siskiyou and Cascade Mountain ranges, offering a scenic view during all four mild seasons. The town has a spectacular network of single-track mountain bike trails that move through the forested mountains and paved bike paths like the Bear Creek Greenway. More accessible walking trails include Lithia Park Loop and Green Springs Mountain Loop Trail.

Ashland will scratch the itch of the more artistically inclined with its annual Shakespeare, as well as Britt evening concerts under a blanket of glistening stars. Travelers can choose between the artistic paradise or the town or try exploring the Klamath Basin, only an hour and a half drive out of the town, home to one of the largest concentrations of bald eagles.


The main street in downtown, Sisters in the summer.
The main street in downtown Sisters, Oregon. Image credit Bob Pool via Shutterstock

Fairytale and small-town charm is what Sisters is all about, with a small population of around 3,000. Part of the Bend, Oregon Metropolitan Statistical Area, the town is a base camp for hiking enthusiasts wanting to scramble the famous volcanic peaks. It will make visitors feel like they traveled back into the 1880s Wild West town, all with the blend of modern conveniences. Drive up through McKenzie Pass, which begins at the town's core, all the way through the Cascades to look over the natural magnificence of the region. The driving tour is bursting with highlights, from the Dee Wright Observatory (built in 1935 amid lava flow), glacial carved-out Suttle Lake, and the aptly named Clear Lake.


West Mooring Basin Marina, next to the iconic Astoria Megler Bridge, Oregon.
West Mooring Basin Marina, next to the iconic Astoria Megler Bridge, Oregon. Image credit Debbie Ann Powell via Shutterstock.com

Astoria is one of the oldest American settlements west of the Rocky Mountains, with close historical ties to the Lewis and Clark Trail, settled at the mouth of the Columbia River. Three scenic rivers close in on steep hillsides, exhibiting quaint Victorian and craftsman-style homes. Eclectic shops, art galleries, restaurants, and the restored 1920s Liberty Theatre all offer visitors a medley of choice once twilight arrives.

Try out the riverwalk, a 6.4-walk tour along the Columbia River on the north side of the town. This tour contains mostly flat and paved surfaces that pass through urban industrial areas and natural environments. Hiking trails like Cathedral Tree to Astoria Column or Coffenbury Lake Trail are also popular, along with mountain biking along the Fort Steens Trail and Crossover Road. Visit the Columbia River Maritime Museum or visit Seaside, Sunset, or Cannon Beach, all of which make visitors believe they've been teleported to a tropical paradise.

Cottage Grove

Currin Covered Bridge near Cottage Grove, Oregon
Currin Covered Bridge near Cottage Grove, Oregon.

Cottage Grove has that sweetness of a small town, spilling with American ambiance, one which many people traveling through the state tend to overlook. With just over 10,000 residents, the community is squished between the Umpsqua National Forest and the Pacific Ocean, a dream that has come to fruition for nature lovers and explorers alike. Visitors adore all six of the romantic covered bridges, all housed within the same area. Make the 30-mile drive, or be bold and adventurous and try it out on a bicycle, where you will travel across Oregon’s first designated scenic bikeway, suitably titled the Covered Bridges Scenic Bikeway. Travel 36 miles across well-kept roads with parks that offer campground and restroom services, such as Schwarz Park and Bake Stewart Park. Take a plunge in the Brice Creek swimming hole in the Umpsqua National Forest and cool off after an adventurous trek. 

Baker City

Aerial view of Baker City, Oregon, on a hazy day.
Overlooking Baker City, Oregon, on a hazy day.

Baker City brims with intriguing tales of the past and more than 100 historical buildings and museums to visit. Visitors can lodge at The Geiser Grand Hotel, built in 1889, or work their educational muscle at the Baker Heritage Museum. Follow along the town's desert landscape on the banks of the Snake River's Brownlee Reservoir at the Farewell Bend State Park.

Do not miss learning about the famed Oregon Trail, which passed through the Powder River and Grande Rone Valleys, over the Blue Mountains, and down to the Columbia River to the Dalles. Explore the Oregon Trail Interpretive Center and learn about the plight of the great migration while observing accurate replicas of the wagons desperate citizens used to haul everything they owned across the great pastures.


Street view in Silverton, Oregon.
Street view in Silverton, Oregon. Image credit Laurens Hoddenbagh via Shutterstock.com

Artistry is the name of the game in Silverton, Oregon. The town blooms with vivid colors at every turn, from the Silver Creek that sneaks through the community and cascades at Silver Falls to the Oregon Garden Resort. Drink in the rousing site of the falls at the ‘crown jewel’ of the Oregon State Park System, with over 35 miles of backcountry trails for mountain biking, hiking, or horseback riding. Try the smooth flow of The Catamount Trail or the Corner to Corner Trail, intended for expert mountain bikers.

Visit ME Horsemanship and get riding lessons, or comb across designated trails. Bathe in tranquility at the Oregon Garden Resort, where a lovely botanical garden encompasses over 80 acres of the property. Fulfill a musing spirit; go antique shopping for collectibles and unique knick-knacks at The Wild Dandelion, Apples to Oranges, and The Old Arcade Trading Company.


Ranch in the adorable town of Joseph, Oregon.
A ranch in Joseph, Oregon.

The beauty of this town is so striking that it became known as the Little Switzerland of America. Joseph is surrounded by the breathtaking Wallowa Mountain range of northeast Oregon, where locals and tourists alike can hike or ride a horse to the summit. The fastest way to get there is to ride the gondola, which rises 3,700 feet from Wallowa Lake Village to the peak of Mt. Howard. Gaze over the soaring scenery at Hat Point Lookout, which features Hells Canyon, the deepest gorge in North America. The climb is rather steep and harrowing, so visitors should only sign on for their adventure if experienced.

Beyond panoramic views, Joseph is the epitome of quaint and poetic, with a series of life-sized bronze sculptures set up along the main street proudly known as the Joseph Art Walk. Shop local at Heidi's Towne Shoppe or Tempting Teal Boutique, specializing in creative and affordable jewelry and clothes. Have a bite at Mad Mary's and top it off at Arrowhead Chocolates for dessert.


Hector Head Lighthouse in Florence, Oregon.
Hector Head Lighthouse in Florence, Oregon.

Adventure abounds in this town on the Central Oregon Coast, located at the mouth of the Siuslaw River. Florence is the perfect amalgamation of what makes Oregon so attractive: the history, the sense of adventure, and the dreamy scenery. Saunter along the coast and visit the many aquatic natural wonders, like the Oregon Dunes (the largest expanse of coast sand dunes in North America), and watch sea creatures frolic at the Sea Lions Caves.

The Heceta Head Lighthouse State Scenic Viewpoint and Light Keeper's Home are a short drive north of downtown Florence on the Oregon Coast Highway. Stay at the Old Town Inn, where you can zoom on dune buggies along the Oregon Dunes National Recreation area, only a few minutes away. (Book directly with Sandland Adventures.)


Azalea Park in Brookings, Oregon, blossoming on a sunny spring day.
Azalea Park in Brookings, Oregon.

Are you looking for a seaside oasis without having to leave the country? Brookings, Oregon, is the place to be. Balmy ocean breezes combined with pristine teal flat waters inspire a mediative essence, with a rugged coastline with sea stacks and rock formations. Explore along the Samuel H. Boardman State Scenic Corridor, which stretches 12 miles of a forested linear park with steep cliffsides and small, sandy beach corners. Admire the 300-year-old Sitka spruce trees as well as the spectacular Arch Rock and Natural Bridges within the corridor. Observe the intertidal rocks and multicolor tide pools of Harris Beach State Park. Visit the Crissey Field Welcome Centre to plan out our ambitious adventure.

Cannon Beach

Aerial View Over Cannon Beach Pacific Ocean Coast Oregon
Overlooking Cannon Beach, Oregon.

Yet another oceanside heaven awaits visitors at Cannon Beach, Oregon, aptly named one of the 100 most beautiful places in the world in 2013 by the one and only National Geographic. Creativity reigns supreme within this little coastal town, with a mixture of art galleries, such as Icefire Glassworks, the Cannon Beach Arts Association, and the Miska Studio Gallery. Beachside relaxation will surely spark the fervent flames of your passion, such as Hug Point, three miles south of Cannon Beach, where, at lower tides, you can walk north and find an oasis of sea caves and a waterfall.

Try surfing the crystal waves in the summer, watch a wild winter storm paint a foggy and eerie image along the shoreline, or muse about the Tillamook Rock Lighthouse, constructed on top of a rock miles from shore in 1880. You will not be able to miss one of the state’s most recognizable landmarks, Haystack Rock, home to kaleidoscopic tide pools and diverse birdlife. Observe glittery starfish and get up and personal with the geological wonder at low tide.

There really is something for everyone in each one of these sweet small towns. So grab a camera, hiking boots, and paintbrush, and step into a world of environmental and historical fascination. 

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