The 9 Most Picturesque Small Towns in Oregon
Oregon represents the wild heart of the Pacific Northwest. Sandwiched between Washington (to the North) and California (to the South) and bordered to the East by Idaho, "The Beaver State" pulls from many scenic ecosystems and ways of life. As such, there is no shortage of quaint, splendid, and gosh-darn-it, downright pretty towns to visit. There are attractive hubs for adventure-seeking youths, solitary sites of refuge for the introspective and/or elderly, trails to hike (a prerequisite across all demographics), mountains to climb, waters to bathe in, and forests to, well, also bathe in! These nine communities should be top of the list of anyone seeking an abundance of aesthetic appeal.
Coos Bay
The harbor city of Coos Bay (sitting on the Pacific Ocean-adjacent bay by the same name) is mysteriously a beautiful waterfront community that is also relatively undiscovered (according to the 2020 census, the population was a mere 15,985). Coos Bay and nearby North Bend and Charleston make up an enriching area known as Oregon's Adventure Coast. In town, there are early-1900s historical buildings to be admired and theaters, shops, and restaurants to be enjoyed, while just outside of the city limits, the Southern Oregon Coastal Wilderness unveils appealing beaches, rugged sand dunes, and forested trails upon which the legendary distance-runner/Olympian, Steve Prefontaine, cut his teeth.
Hood River
Hood River is nestled on the banks of the titular waterway and the substantial Columbia River, which defines part of Oregon's border with Washington. This 8,313-resident city is considered the windsurfing capital of the world. Find a spot on the Columbia River Gorge to watch scores of adrenaline-hungry characters harness the power of nature while in the shadow of snow-capped Mood Hood (Oregon's highest peak) and other extensions of the stunning Cascade Range. Hood River is also no exception to Oregon's hiking-fostering ways and also encourages bikers and ski bums to get after it. Visitors to Hood River Valley will also delight in the "Fruit Loop," a stretch of 27 farmside fruit stands, wineries, breweries, and/or flower fields.
Ashland
Just 16 miles North of the California border, in Southwestern Oregon, Ashland invites admirers of beauty, both natural and designed. Situated at the base of the Siskiyou and Cascade mountain ranges, the rich scenery inspires the artist within. In fact, this Jackson County community has been voted one of the best small art towns in America. Perhaps the biggest draw is the 82-year-old Oregon Shakespeare Festival which offers regular theatrical performances by dedicated Thespians. For those searching for alternative muses, Ashland also has award-winning galleries displaying evocative exhibits, top-tier restaurants to satisfy all food lovers, and artisanal shops to uncover.
Bend
One of the most picturesque towns in Oregon (well, to be fair, it's a moderately-sized city) is also one of the prettiest desert towns in all of America. Within the unique landscape of Oregon's High Desert sits the former logging town of Bend. The extensive and alluring trail network (51 miles are immediately accessible while others head off into the mountainous wilderness, led Bend to become a host of the Mountain Running National Championships and to garner the title of "America's Best Trail Running Town" by Outside magazine. But running is not the only game in town. With an average of 300 sunny days per year, there is always an excuse to get outside and enjoy the community (floating down the Deschutes River is another popular pastime).
Cottage Grove
Cottage Grove, the name alone, conjures pleasant imagery. This sub-11,000-resident city rests in Lane County, just South of Eugene. Twice it has been awarded the "All-American City" honors, owing to a mixture of wholesome traits. For starters, this extremely bike-friendly community encourages one to pedal away a Saturday afternoon on the 37.8-mile Covered Bridges Scenic Bikeway (i.e., the largest collection of such structures in the Western United States). This led to another informal but adorable title of "the covered bridge capital of Oregon." Cottage Grove is also known for its picturesque waterfalls, its filming locations from several well-known features, outdoor murals, live-music venues, and all the classic charms of an all-American community.
Astoria
Further West along the Columbia River, just before it meets the Pacific Ocean, is the small port city of Astoria – the oldest settlement West of the Rocky Mountains. Ripples from this fishing village's past continue to emanate and build upon the plethora of Victorian-era homes to create a charming historical essence. Add in a crafty but simple downtown strip, seaside restaurants, deep green hillsides, and the Astoria-Megler Bridge that connects to the Washington shore, and Astoria looks like a pretty appealing package. Other nearby highlights include the hilltop Astoria Column, complete with murals depicting local history, and the Lewis and Clark National Historical Park, which is divided from Astoria by Youngs Bays.
Cannon Beach
A skip South down Oregon's wondrous coastline and Cannon Beach (the name of the resort community and the magnetic sandy stretch) reveals a blend of wild and pristine nature. Sunbathers, surfers, hikers, and even seaside equestrian buffs gather in these parts to appreciate the trifecta of flat sands, a rugged, sheltering coast, and the dramatic rock formations that sprout skywards in the first shallow section of the ocean. The most prominent statue is Haystack Rock, which welcomes flocks of adorable tufted puffins each spring. Regardless of the time of year, hike up to the breathtaking viewpoints at Ecola State Park, or bop over to Hug Point, to explore sea caves during low tide (just keep an eye on the time!).
Woodburn
Woodburn is a colorful spot that nearly splits the distance between the happening city of Portland and the state's capital city of Salem. The best time to stop by for a visit is in the spring, for between mid-March to May, the Wooden Shoe Tulip Farm is in full bloom. Walking onto this property is like wandering into a painting. The gigantic floral arrangement, punctuated by a cute pink tractor and red windmill, creates a stimulating palette that is tough to beat. Next up, treat yourself to a hot air balloon ride for a brilliant panorama of Northern Willamette Valley (i.e. Oregon's wine country – complete with over 700 fertile wineries).
Yachats
Ending our journey of pretty Oregon towns is one last coastal community, this time in Lincoln County, an hour and a half drive North of Coos Bay and about double that South of Cannon Beach, Yachats. The name of the town and the river that runs through it, pronounced YAH-hots, is derived from the Indigenous Siletz language and means "dark water at the foot of the mountain" – a concise description if there ever was one, given that this area is sandwiched between the verdant Oregon Coast Range and the black basalt-lined Pacific Ocean. Grab those hiking boots one last time and grunt your way to the Cape Perpetua Overlook – an awe-inspiring view at the highest point in these mountains.
The jury-rendered verdict, peer-reviewed evidence, and anecdotally-supported opinions equally conclude that Oregon has it all. If you seek the strength of the mountains, the wisdom of the ocean, the healing ways of the forests, or the energy of a passionate community, there are towns for any and all of those. These nine pretty places will give you an impactful overview of the state, and connecting all the dots will blow your socks off even more.
