The Most Underrated Towns In Oregon
Oregon has something for everyone. Portland’s great music, quality food, and endless cultural offerings. Newport’s classic seaside charm. Cannon Beach’s famous Haystack Rock. But what you may not know is that the Beaver State has a wealth of lesser-known small towns with unique appeal. You can gaze out at the Pacific Ocean and explore the rugged coast without fighting the crowds. You can taste your next favorite wine, bask in the lush landscape, and cheer for your next favorite band no one’s ever heard of. It’s all within your reach if you take the time to check out the most overlooked towns in Oregon in 2025.
Jacksonville
Jacksonville is a National Historic Landmark town with over 100 buildings on the National Register of Historic Places. Walk down Oregon Street, and you are transported into the gold rush era, with excellently preserved 19th-century Victorian architecture surrounding you. All summer long, the Britt Music & Arts Festival hosts diverse, world-class concerts at a naturally formed amphitheater, the Britt Festival Pavilion.
Or, if you’re visiting around Christmas time, the town’s festive Victorian Christmas celebration has holiday lights, trolley tours, hot apple cider, and a Victorian parade. Any time of year, visit the first-rate Beekman House museum to immerse yourself in the town’s history and culture.
Joseph
Joseph sits in the shadow of the magnificent Wallowa Mountains, which lend their grandeur and beauty to the town’s culture. The Joseph Art Walk, on Main Street, showcases life-sized bronze sculptures by renowned sculptors, plus you can stroll the cobblestone sidewalks and duck into the many art galleries. Next, head over to Wallowa Lake and ride the Tramway to the top of Mount Howard, where you’ll see why they call Joseph “Little Switzerland” — the surrounding mountains look like the Swiss Alps.
For more cultural appeal thereafter, head to the Josephy Center for Arts and Culture. In 2025, you can check out the Steve Arment Woodcarving: From Tree to Tale Exhibit, which will run until December 18. You’ll get to see a range of whimsical, intricate folk-art woodcarvings.
Baker City
Baker City offers a snapshot of eastern Oregon, so much so that it’s known as “the base camp for Eastern Oregon.” You’ll want to at least see the Geiser Grand Hotel, a Victorian building that was built in 1889. It has an elegant restaurant that features an ornate stained-glass atrium, washing the dining room in light. Speaking of restaurants, top-rated Barley Brown’s Brewpub has award-winning beers and a best-of-the-best pub food menu. A warm and welcoming pub like Barley Brown’s offers the perfect cap to a day on the slopes at Anthony Lakes Mountain Resort, which is located west of town in the Elkhorn Range of the Blue Mountains.
Back in town, Geiser Grand’s owner-operator, Ron Colton, offers horse-drawn tours through downtown. According to Barbara Sidway, Colton’s partner, “Baker City is the largest intact 19th-century streetscape in the American West. There are more than 100 buildings on the National Registry of Historic Places, so this tour is like visiting a museum of Victorian architecture. The horses provide the perfect pace to get to know it.”
Gold Beach
Gold Beach is a well-kept secret where the Rogue River empties out into the Pacific. You can hop on a jet boat and hurtle over Rogue River whitewater, courtesy of Jerry’s Rogue Jets, from May through October. In Gold Coast, you’re near the one-of-a-kind Prehistoric Gardens, a lush rainforest park 17 miles to the north with 23 life-size dinosaur statues among the dense foliage. On the beach, you can see the sunset of a lifetime at Kissing Rock, a famous rock formation. Bailey Beach and Myers Beach have ample razor clams you can hunt for with a trowel. Or rent a crab ring from Rogue Outdoor Store and go crabbing for Dungeness crabs.
La Grande
La Grande is a lively little university town with tons of scenic and cultural attractions. At Ladd Marsh Wildlife Area you can catch sight of numerous wetland birds flitting in and out of the cattails. The Ladd Marsh Bird Festival in May features music, presentations from biologists, artists doing plein air pieces, and guided birding expeditions. If you want a glimpse of pioneer history, Oregon Trail Interpretive Park in the Wallowa-Whitman National Forest has great hiking and signs that tell the tale of emigrants crossing the Blue Mountains. After a day of exploring, rest and soak at The Lodge At Hot Lake Springs, a former sanatorium that is now a hotel. You can warm up in the hot springs, watch a movie in the theater, and grab refreshments at Thermal Pub & Eatery next door.
Cottage Grove
Cottage Grove is in the land of the covered bridges. There are more covered bridges on the beautiful 20-mile Cottage Grove Covered Bridge Tour Route than there are anywhere else out West. Once you’re done biking or driving the route, a self-guided tour of downtown reveals amazing murals. These include the Buster Keaton mural on the old Cottage Grove Hotel building, which commemorates the filming of The General (1926) in Cottage Grove, starring—you guessed it—Buster Keaton.
Next, no one will blame you for chasing waterfalls. The Row River Waterfall Corridor has six waterfalls within driving distance of Cottage Grove. Don’t miss the amazing Moon Falls, which plummets for 125 feet. The hike is only half a mile. Finally, for a taste of Cottage Grove culture, check out the Art Walk, happening December 26 in 2025.
Milton-Freewater
If you want a taste of Oregon’s bounty without waiting in line, Milton-Freewater is the ticket. Here in the "Rocks District" American Viticultural Area (AVA), the wine flows like water. The Watermill Winery in town is the perfect place for tasting a great selection of estate wines, Blue Mountain cider, and select beers.
You can indulge your taste buds further at Petits Noirs, a boutique chocolate shop with handmade truffles, drinking chocolate, and so much more. Petits Noirs is on the Whisky & Rocks Farm Loop, an epic self-guided tour of 25 farms, orchards, wineries, and artisan makers of all-things-delicious. Finish off your Milton-Freewater experience with a tour of the Frazier Farmstead Museum and learn everything you need to know about this fertile, underrated gem of a town.
Fossil
If you’ve never been to the John Day Fossil Beds National Monument, the town of Fossil is your launch point. Entrance to the monument is free and there are three different areas to explore, including the Painted Hills Unit with its incredible bands of crimson on the hillside. Here in Fossil, you will unearth a truly Western landscape of desert rock, windswept vistas, and a dark night sky where the only lights you see for miles are stars.
You can even try your hand at digging for fossils at the Wheeler High School Fossil Beds—you keep what you find. For events, the Wheeler County Bluegrass Festival (July 3-5, 2026) is a surefire bet, as it’s free. What’s more, the Wheeler County Fair & Rodeo in August is a blast for any lover of down-home Western culture.
Find Oregon’s Underrated Treasures
Your next trip to the Beaver State can reveal little-known gems that most tourists haven’t discovered. The coastline in its sheer majesty sprawling before your eyes, the untrammeled backroads and romantic covered bridges, the open fields as the golden sun sinks into the horizon. Plus, these towns represent America’s cultural roots. Oregon’s most underrated towns furnish opportunities to slow down and enjoy the most delicious a slice of American pie you’ve ever had.
