The Most Picturesque Small Towns in Oregon
When you look at the Pacific Northwest of the United States, Oregon is comparatively less favorable than its neighbors like California, Washington, and Nevada. Nevertheless, you must travel the state in search of picturesque small towns beckoning with their charming main streets, historic architecture, and breathtaking scenery. In the light of metropolises like Salem and Portland, these towns showcase the very essence of the Oregonian spirit via artistic enclaves that nurture creativity in the historic settlements, echoing the tales of pioneers.
Be it the seaside likes of Cannon Beach with its incredible Haystack Rock or inland gems like Joseph giving access to the Wallowa Mountains, it is undeniable that these following 10 towns are against the backdrop of some of the most beautiful scenery in the country.
Astoria
Astoria’s charming Victorian architecture, epitomized by the Flavel House Museum, adds a timeless allure, making it a visual treat for visitors at the mouth of the Columbia River. While you can admire the lifestyle of the 19th century in the Flavel House, the beautifully restored venue of the Liberty Theatre has been hosting concerts, plays, and films since 1925.
Those looking for something different on this trip will love the Cathedral Tree Trail. This lesser-known hike leads to a massive, ancient Sitka spruce, known as the Cathedral Tree, in its about a mile journey. You can also hop on the Astoria Riverfront Trolley, a charming, old-fashioned 1913 trolley car that offers a narrated tour along the waterfront.
Baker City
Baker City is a picturesque small town in the Blue Mountain foothills that takes pride in its—well-preserved 19th-century architecture. The Historic Baker City district is a treasure trove of Victorian-era buildings, with the Geiser Grand Hotel standing as a stunning centerpiece. This opulent hotel, built in 1889, features intricate mahogany woodwork and stained glass, making it a must-see for architecture enthusiasts.
Baker City's natural surroundings are equally captivating. The close proximity to the Elkhorn Mountains gives access to the Elkhorn Crest Trail. The 20+ miles path bestows hikers with beautiful views of alpine lakes, wildflower meadows, and rugged peaks.
Hood River
Hood River's setting, against the backdrop of Mount Hood and along the banks of the Columbia River, provides endless opportunities for outdoor recreation and breathtaking views. Water sports enthusiasts flock to Hood River for its world-class windsurfing and kiteboarding conditions. The Columbia River’s steady winds create ideal conditions and several local shops like Gorge Wind Guide Services and Big Winds Hood River offer rentals and lessons for beginners. For a more relaxed experience, take a paddleboard or kayak out on the river.
About 12 miles away, you will find the Punchbowl Falls County Park. This secluded park features two stunning waterfalls and swimming holes along the Hood River. The trail to the falls is ideal for a peaceful hike through lush forests, making it a perfect escape from the busier tourist spots.
Jacksonville
Jacksonville, a beautifully preserved Gold Rush-era town in the Rogue Valley, is one of Oregon’s most picturesque small towns. While, the Jacksonville Inn, a historic hotel dating back to 1861, is a great place to stay or dine, it is also a prominent downtown landmark. Next, you must stop by the Beekman Native Plant Arboretum. Located behind the historic Greek-revival-style Beekman House, this arboretum features a diverse collection of native plants, providing a peaceful and educational escape. The Beekman House itself, once home to one of the town’s wealthiest pioneers, is open for tours and gives a fascinating glimpse into the opulent lifestyle of Jacksonville’s early residents.
Alternatively, the Jacksonville Woodlands is a natural gem. This extensive 15+ miles of trail system winds through 320 acres of protected woodlands, providing hikers scenic views of the town and surrounding countryside. The trails are well-marked and range from easy walks to more challenging hikes, making them accessible to all levels of outdoor enthusiasts.
Joseph
The Wallowa Mountains town of Joseph is a visual delight best experienced at Wallowa Lake, a pristine body of water ideal for boating, fishing, and paddleboarding. The lake is framed by stunning mountain peaks, making it a photographer's paradise. Riding on the Wallowa Lake Tramway to Mount Howard's summit, one of the steepest tramways in North America, for the lovely scenery of the Wallowa Valley and Eagle Cap Wilderness, is another option.
The town's main street is lined with charming galleries and bronze sculptures, reflecting its reputation as an artist’s haven. One of the standout landmarks is the Josephy Center for Arts and Culture, which showcases local artwork and offers workshops for aspiring artists. Also stop by the Embers Brew House, where you can enjoy locally brewed craft beer and wood-fired pizza in a family-friendly setting.
Yachats
Yachats- the “Gem of the Oregon Coast" on the edge of the Pacific Ocean strikes the right balance between rugged beauty and vibrant community spirit. When outdoors you will find the Cape Perpetua Scenic Area is the biggest attraction. This expansive 2700 acres of natural area features old-growth forests, dramatic coastal vistas, and the Devil’s Churn, a narrow inlet where waves crash with mesmerizing force. The Cape Perpetua Visitor Center upholds educational exhibits and guided walks, providing insights into the region’s unique ecology.
Yachats’ cultural scene is equally enchanting. The annual Yachats Mushroom Festival celebrates the region's rich fungal diversity with guided hikes, cooking demonstrations, and tastings. You cannot skip the Luna Sea Fish House when in town. The restaurant’s fish and chips, made from the catch of the day, are a hit among locals.
Sisters
The charming downtown of Sisters where wooden sidewalks and Western-style storefronts evoke a bygone era. The Sisters Art Works entertains with art exhibits, workshops, and live performances, reflecting the town’s strong artistic spirit since 1977. For dining, the Open Door Wine Bar is among the top options, with local wines and farm-to-table dishes. Sisters Bakery, a local institution, serves delicious pastries and baked goods, perfect for a morning treat.
Meanwhile, the Peterson Ridge Trail System is well-maintained and less crowded than other popular outdoor spots. This extensive network of trails has stunning views of the Cascade Mountains and the Deschutes National Forest, providing opportunities for hiking, mountain biking, and horseback riding.
Cottage Grove
The "Covered Bridge Capital of Oregon," Cottage Grove, takes pride in its small-sized yet picturesque community. The Row River Trail, an almost 16-mile path perfect for biking and hiking, is another highlight. This trail winds through forests, meadows, and alongside Dorena Lake, offering picturesque views at every turn. Along the way, you will pass the famous covered bridges that the town is known for—like the Chambers Railroad Bridge, the only remaining covered railroad bridge in Oregon.
Moving on, a walk through the Historic District will take you to the Cottage Grove Museum, housed in a former 1897 church. The museum showcases local artifacts, from Native American relics to pioneer-era tools, providing a deep dive into the town’s past. The 1982 Cottage Theatre, which hosts performances ranging from musicals to dramas throughout the year is also an appealing spot.
Cannon Beach
The iconic Haystack Rock, a towering 235-foot sea stack rising from the ocean, is a natural landmark that epitomizes Cannon Beach’s rugged beauty. At low tide, the area around the rock reveals vibrant tide pools filled with starfish, sea anemones, and other marine life. The beach is also a perfect spot for a relaxing walk, kite flying, or soaking in the breathtaking ocean views.
The town itself is a haven for art lovers, with numerous galleries showcasing local artists' work. The Icefire Glassworks is particularly notable, offering a range of fine art and glass creations. You may plan to visit the annual Cannon Beach Sandcastle Contest, a fun and competitive event that draws talented sand sculptors from near and far since 1964. Dining in Cannon Beach is a treat, with plenty of options to suit all tastes. The Wayfarer Restaurant comes to list for its fresh seafood whereas try the Pelican Brewing Company, where you can enjoy craft beers and hearty pub fare.
Silverton
Straight in Willamette Valley's heart, you can head to Silverton, known for its beautiful gardens, charming downtown, and proximity to stunning waterfalls. The most apt evidence is the Oregon Garden, an 80-acre botanical garden featuring a diverse array of themed gardens, including the stunning Rose Garden, the whimsical Children's Garden, and the therapeutic Sensory Garden. The garden also houses the Gordon House, the only Frank Lloyd Wright-designed home in Oregon, offering guided tours that delve into the architect's innovative designs.
Meanwhile, you can admire Silverton's captivating art scene through its numerous galleries and public art installations. The Lunaria Gallery, a cooperative gallery run by local artists, has a wide range of artwork from paintings to sculptures. You can also check out the Silverton Country Museum recounting the local history through exhibits like historic photographs, pioneer artifacts, and a detailed model of the town.
Oregon’s small towns are like bubbling pots brimming with unique charm and vibrant cultural experiences. Whether it is the tranquil shores of Yachats, the lively arts scene in Joseph, or the Western-inspired charm of Sisters, each town presents a unique slice of Oregon life. These towns invite you to slow down, appreciate the beauty around you, and discover the hidden treasures that make Oregon such a uniquely enchanting place boasting some of the picturesque destinations in the Pacific Northwest.
