When the weather gets chilly, take the opportunity to hit the road in Oregon, where you’ll find fewer crowds and more affordable lodging options. Cuddle by the fire with a glass of wine, forge into frosty or fog-kissed wilderness, or see some of the best art and culture in the state. Here are suggestions for a trip in every region that allow you to fully embrace an Oregon winter.
Outdoor Adventures Across the State
Oregon’s outdoor activities don’t stop when the weather gets cooler — they just get more awesome. In Central Oregon, Paulina Lake Lodge & Resort in Newberry National Volcanic Monument is under new ownership. It’s a great place for a car-free trip so you don’t need to drive in the snow. Leave your car at the 10-Mile Sno-Park parking lot and catch a 20-minute ride on the Lodge’s Snow Bus. The bus will haul you and your gear to a lakeside log cabin, fully equipped with a kitchen and fireplace. Snowshoe and cross-country ski right out your door, working up an appetite for prime rib and homemade cobbler in the rustic 1929 lodge, open for dinner Thursday through Sunday.
Make Baker City your home base for an Eastern Oregon winter escape. Stay at the elegant Geiser Grand Hotel and stroll downtown for shops or a cinnamon roll at Sweet Wife Baking. For dinner stop by historic Barley Brown’s Beer for a pint and comfort food, or dig into a burger with onion rings at budget-friendly Oregon Trail Motel & Restaurant, where the classic diner vibe is paired with hunting trophies on every wall. You can hit the slopes and book an overnight in a cozy yurt at charming Anthony Lakes Mountain Resort — 35 miles northwest of Baker City in the Blue Mountains — or spend the day sledding with the family in the Anthony Lakes area.
On the Oregon Coast, an escape to the Nehalem Bay area also offers plenty of outdoor fun. Watch crashing surf on Manzanita Beach, or ramble around Nehalem Bay State Park for ocean or bay views and bird-watching. Take a half-mile walk through lush ferns and moss-draped trees to Short Sand Beach in Oswald West State Park — the best time of year to see fewer people and more wildlife. Overnight at the historic Old Wheeler Hotel and refuel at The Salmonberry, offering creative wood-fired pizzas overlooking the Nehalem River.
Sip Wine During Cellar Season
Cellar season each winter is prime time to visit Oregon’s renowned wine regions. With the vineyards inactive, welcoming owners and winemakers have more time to chat about their vintages.
In the Willamette Valley, plan a wine-tasting getaway with a stay in a restored antique travel trailer at The Vintages Trailer Resort in Dayton. It’s worth checking out small towns like Carlton, where you can sample wine from a dozen-plus vintners at The Carlton Winemakers Studio. Carlton Bakery is nearby on Main Street, along with The Horse Radish, Blind Pig and eight tasting rooms.
The wineries of Southern Oregon also make for an inviting trip during cellar season. Book one of the chic rooms at historic Kubli Haus in Jacksonville. Tour nearby Applegate Valley for wine tasting; and visit Troon Vineyard, known for its biodynamic wines, and Valley View, where Oregon’s first wine grapes were planted in the 1850s. Dining options in town include Bella Union for pizza, pasta and live music on weekends, as well as Cowhorn Kitchen & Wine, with a menu crafted from ingredients farmed locally.
Enjoy Culture and Cuisine in Beautiful Places
For the perfect urban getaway, head to Portland for a multiday trip filled with art, culture and a dynamic food scene. You’ll find casual yet upscale accommodations at The Hotel Zags downtown. For outdoor fun, borrow equipment from the hotel’s gear shed, including bikes, binoculars and more. Spend an afternoon at the newly expanded Portland Art Museum, just a six-block stroll away. Discuss your insights at the museum’s new Coquelico cafe, a modern European-style bistro offering breakfast, lunch and dessert inspired by exhibitions; or try nearby Nuvrei bakery, where decadent pistachio-rose croissants may accompany your coffee. For dinner opt for budget-friendly Szechuan dishes at Duck House, or splurge at Portland’s legendary farm-to-table restaurant Higgins before heading to a concert or event downtown.
While many visitors check out Hood River for winter sports and the Columbia River Gorge National Scenic Area, winter is also the perfect time to see local art and culture. Boutique lodging makes for a cozy weekend. Consider the new Lightwell Hotel with stunning rooms, a full-service spa and multiple dining options. Downtown Horsefeathers Hotel features intimate condo-style accommodations in a restored 19th-century building. There’s plenty of art to see nearby — including local artist collectives Made in the Gorge and 301 Gallery — and a self-guided walking tour of outdoor sculptures. History buffs can learn more about the area’s Mexican and Japanese American heritage at The History Museum of Hood River County.
