: Stirling Cobb

Winter Trips in Central Oregon

October 17, 2019

The sunny, high-desert landscape of Central Oregon brings happiness in myriad ways. There’s the sandy, rolling single-track beloved by mountain bikers and the bluebird skiing that draws powder hounds to the slopes of Mt. Bachelor. Old West enthusiasts come for small-town rodeo and historic sites, while beer lovers converge for the craft beer created from the clean river water and locally grown hops. In the wintertime, the High Cascade peaks draw the frosty marine air off the Pacific Ocean for a marriage that results in champagne powder, and that’s the perfect foundation for winter fun. From skiing and snowshoeing to tubing, fat biking, sleigh riding, beer tasting and more, here’s what to do in Central Oregon this winter.

Nordic skiing at Mt. Bachelor (Photo by: Nate Wyeth)

Snow Sports for All

Ski or board the steeps, deeps and trees of Mt. Bachelor ski area’s 101 runs, where 3,365 feet/1,026 meters of vertical drop on 4,300 acres/1,740 hectares of skiable terrain make up one of the six biggest ski areas in the nation. Bachelor’s Snowblast Tubing Park is a thrilling, 800-foot/244-meter ride down six speedy lanes, and the mountain offers the longest groomed Nordic skiing season in the U.S. with trails open from mid-November into May. Snow bunnies of all ages can try a free guided snowshoe tour, a lovely way to experience the winter wonderland at a slower pace. The nearby Meissner Nordic trail system offers 25 miles/40 kilometers of groomed trail for classic and skate skiing. And for those who’d rather play with snowballs than catch air, a number of sno-parks around the region provide backcountry access to powdery bliss. If your pup loves to romp through the white stuff, Wanoga, Edison Butte and Skyliners sno-parks are dog friendly (just remember to pick up after your pets and leave these places cleaner than you found them for everyone to enjoy). For fat-tire fanatics, check out local bike shops for lessons and rentals for the new snow-biking craze. Alter-abled adventurers can sign up with Oregon Adaptive Sports for accessible skiing and snowboarding lessons at Mt. Bachelor and Hoodoo Ski Area.

Sunriver Nature Center & Observatory

Family-Friendly Discoveries

North from Bend, the high-desert hamlets of Redmond, Terrebonne and Prineville have the cure for cabin fever, with family-friendly activities that will get you moving outside. Get some fresh air while exploring the Redmond Caves Recreation Site (open year-round), formed thousands of years ago when a lava tube collapsed and created five caves from the molten lava of the Newberry Caldera. For rock climbers and hikers of all ages,  Smith Rock in Terrebonne is stunningly beautiful in winter, with trails of varying distances and difficulties. Set at the foothills of the Ochoco Mountains, Prineville is a treasure trove of natural wonders with lots of history, too. Learn about the colorful characters and fascinating artifacts dating back to the 1850s that helped shape this region at the A.R. Bowman Museum, located in an old bank building. The High Desert Museum in Bend, the Sunriver Nature Center & Observatory and the Wizard Falls Hatchery in Camp Sherman offer awe-inspiring encounters with local wildlife. While you’re in the area, take time to tap into Central Oregon’s lauded craft-beer scene, with family-friendly fare at Wild Ride Brewing in Redmond, Mystic Roots Brewing Co. in Terrebonne and Ochoco Brewing Company and Crooked River Brewing in Prineville. 

Bend's Old Mill District

Arts, Culture and Boutique Explorations

Set amid the rural beauty of the high-desert plains and soaring Cascade Mountain peaks, the urban-leaning outpost of Bend offers fine cuisine, one-of-a-kind boutiques and a vibrant nightlife. Browse downtown shops like Hot Box Betty and Revolvr Menswear for the best in mountain chic. The Box Factory is an enclave of craft food and drink outposts including the Humm Kombucha tasting room, and the Old Mill District offers scores of national-brand shops. Taste the beer that helped launch Oregon’s craft-beer revolution at Deschutes Brewery — just one of 25 stops along the Bend Ale Trail. Fine brews complement the region’s growing culinary tradition with offerings like Bos Taurus, a boutique upscale steakhouse, and the town’s oldest local diner, The Pine Tavern. Jump into the happening music scene with shows at The Domino Room and all-ages performances at McMenamins Old St. Francis School. Arts lovers rejoice — there’s a vibrant cultural scene here. The Tower Theatre hosts shows all year round, as does OperaBend and High Desert Chamber Music. Slide into a booth for live jazz in the evening at the swanky Oxford Hotel downtown, and spend the next day browsing the world-class collection of local works downtown known as the Tin Pan Alley Art Collection. Beyond Bend, find a vibrant enclave of boutiques, galleries and venues for music in the Old-West town of Sisters. Hood Avenue Art Gallery in Sisters is a hub not just for visutal art but also music and theater events several times per year. In nearby Sunriver, Artists Gallery is a co-op of 30 local artists’ mixed-media work — a place to shop for affordable art or channel your creative efforts with an artist-led class. 


If You Go:

While you’re out adventuring in Central Oregon’s pristine wild spaces, consider giving back by supporting Bend’s Pledge for the Wild. Text WILD4BEND to 44321, which lets you make a small donation of a dollar per hour of free recreation you just enjoyed to the Deschutes Trails Coalition. Before you travel, know that the mountain roads leading to Central Oregon are often snowy, icy and slick, with chains required for vehicles in winter months. Check road conditions and conditions at the sno-parks before you head out. Or think about making a car-free trip to truly sit back and enjoy the ride. Winter in Oregon can be unpredictable, so come stocked with fuel, extra food, water and emergency supplies, and brush up on How to Winter Like an Oregonian.

Snow Sports Itinerary


Family Fun Itinerary

Redmond, Terrebone, Prineville, Bend, Sunriver, Camp Sherman

Arts and Culture Itinerary

Bend, Sisters, Sunriver

About The

Jen Anderson
Jen Anderson is a longtime journalist and travel writer/editor who is now Travel Oregon’s Content & Community Manager, helping to align content for visitors via social media, print and web. She’s called Oregon home for 25 years and loves finding the latest places to eat, drink and play around the state with her husband and two boys. Brewpubs, beaches and bike trails top the list.

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