7 Coziest Mountain Towns In Oregon

With at least 50 named mountain ranges, Oregon makes it easy to find a picturesque mountain town. The Cascades, Blue Mountains, and Wallowas are just a few ranges where you can hike, raft, or camp, appreciating the state’s incomparable beauty. In their valleys, meanwhile, you will find small towns that feel especially cozy with English-style pubs, scenic wineries, antique shops, and orchards, setting you up for an unforgettable fall season this year.

Oakridge

Oakridge sits in the foothills of the Western Cascades at 1,200 to 1,700 feet in elevation, enjoying some of the region’s best weather: high enough to escape the fog yet low enough to avoid the heavy snow of higher elevations. There are plenty of natural attractions in the surrounding areas, such as Salt Creek Falls, which sits about a half hour southeast of town and is one of the tallest single-drop waterfalls in Oregon, plunging 286 feet. After your waterfall hike, head back in town to grab a craft beer at the 3 Legged Crane Pub and Brewhouse, a cozy English-style pub that hosts live music performances on Fridays and Saturdays. You can settle in for the night at the Arbor Inn Motel, an updated, vintage-style motel with friendly staff and comfortable rooms.

Ashland

Perched near where the Siskiyou Mountains join the Cascades, Ashland is surrounded by lush green beauty. There are countless hiking trails to explore in the area, such as the Pacific Crest Trail, which meanders within roughly 100 yards of the Mt. Ashland summit, beginning from the Mt. Ashland parking lot. Also part of the Rogue Valley Wine Country, seven vineyards are nearby to visit during your stay! There is plenty to experience at the Belle Fiore Estate Winery, an Italianate-style winery, including a paviolin tasting room, terrace restaurant, and tours of the chateau and vineyard. Irvine & Roberts Vineyards is another beautiful winery to add to your itinerary, offering panoramic views of the mountains and vineyards from the tasting room.

Enterprise

Travelers will fall in love with Enterprise, an old-fashioned, pioneer-spirited town in the Wallowa Mountains. To take in the region’s vintage character, embark on the Wallowa County Barn Tour, which highlights nearly 30 historic barns. Several stand within Enterprise’s city limits, including Harmon Barn, Sunrise Iron, and Mawhin Barn. Seeking an old-timey souvenir? You will almost certainly find one at Favorite Finds on Main, a local antique shop that has antiques dating back as far as the 40s, 50s, and 60s. Golfers can admire the town’s mountain views at the Alpine Meadows Golf Course, a nine-hole layout where Trout Creek winds along the fairways.

Joseph

Just 10 minutes down the road from Enterprise, travelers will find Joseph, an artsy mountain town that is also in the Wallowa Mountains. For unbeatable mountain views, start your journey in Joseph with a ride on the Wallowa Lake Tramway, which ascends 3,700 feet to the summit of Mt. Howard in less than 15 minutes! The town’s art scene is just as impressive as its mountain views, showcased along the Joseph Art Walk, where massive bronze sculptures reflect the area’s Western heritage. To appreciate some artisan work, stop by The Sheep Shed as well, which sells upscale, hand-painted yarns, handwoven items, jewelry, and art cards.

Hood River

Just an hour east of Portland, in the Cascades, Hood River has become one of the most beloved mountain towns in northern Oregon. There are all kinds of recreational activities to enjoy year-round. One of the best places to take it all is the Cooper Spur Mountain Resort, a peaceful property surrounded by pines, meadows, and rushing waters. It is popular for its hiking, biking, rafting, and kayaking opportunities. There are also several orchards and farms to visit in the area, for those interested in the town’s agritourism scene. With fall approaching, Packer Orchards is a wonderful place to add to your list, offering fall fun like a pumpkin patch, a corn maze, fresh apples and pears, an activity field, and various fall-themed pastries. Make sure to visit one of Hood River’s renowned breweries while in town as well! Double Mountain Brewery is a local favorite, serving craft beers, dry ciders, house-made non-alcoholic root beer, and ginger ale.

Baker City

Baker City is located near the Wallowa-Whitman National Forest, the Elkhorn ridge of the Blue Mountains, and the Wallowa Mountains, resulting in abundant hiking trails, campsites, and other recreational areas. Travelers wanting to spend the weekend immersed in the mountain air can pitch their tent at the Anthony Lake Campground, which sits at an altitude of 7,100 feet and overlooks Anthony Lake. The town was also once an important part of the Oregon Trail, with visitors able to explore this history at the National Historic Oregon Trail Interpretive Center, which is set on a hillside, offering interactive exhibits, large displays, and a replica wagon camp. Hungry travelers can head downtown to grab a bite at Inland Cafe, a locally cherished restaurant that serves all kinds of American favorites.

Estacada

Estacada makes another convenient weekend getaway from Portland, set in the Cascade foothills along the Clackamas River. Known for its agritourism, it has even earned the nickname “Christmas Tree Capital.” Travelers can experience the town’s thriving agricultural scene at the Hillockburn Farm, a boutique farm that grows produce and flowers while crafting artisan goods like blueberry spread and honey. From May through September each year, the town hosts a weekly farmers market on Saturdays, promoting the community’s local farmers and craftsmen. Those hoping to get out in nature can explore Milo McIver State Park, a scenic park with opportunities for camping, kayaking, canoeing, rafting, fishing, hiking, and horseback riding.

With autumn in full swing, cozy moments are hard to resist. And what could make fall cozier than a trip to one of the state’s adorable mountain towns? Whether you want to go vineyard hopping in Ashland, camping in Baker City, or pick a pumpkin from the pumpkin patch in Hood River, there are many options for this season. All you have left to do is choose a town and see where the adventure takes you!