: Courtesy of Mt. Bachelor

5 Epic Ways to Winter in Bend

Kimberly Bowker, Guest Author
December 13, 2018

We all know winter in Bend means endless downhill skiing and snowboarding. But the seasonal fun doesn’t stop at the slopes. Sledding, songs, shopping and more — here are five ways to live it up in Bend this season.

Desert sky in the Badlands by Christian Heeb

1. Winter like you summer: Climb, hike and bike the trails

When the air is crisp and the sun is shining, get outside and hit the high-desert trails — but be sure to always be idea mindful of trail conditions and ice. Head east for a hike through an ancient Juniper forest at the Oregon Badlands Wilderness, or catch a view walking up Horse Butte or mountain biking Horse Ridge. Travel north to the Maston trail system for mountain biking and trail running, and continue to Terrebonne and Smith Rock State Park, where the most commonly used trails in winter are the River Trail, Wolf Tree Trail and Rim Rock Trail.

Courtesy of Zydeco Kitchen & Cocktails

2. Treat yo’self: Good eats and drinks

When hunger calls, there’s no lack of great grub in Bend. Savor a steaming cup of coffee in the little bungalow that houses McKay Cottage Restaurant — a local favorite known for their creative spin on an eggs benedict, with pork sausage patties and poached eggs atop a homemade soft pretzel. Another brunch hotspot is The Victorian Café; be sure to gather around the outdoor fireplace with their signature bloody Mary, which comes with a giant skewer of over-the-top garnishes such as smoked prawns, Andouille sausage, pepper-jack cheese and pepperoncini. Drool-worthy dinner spots include Cajun-Northwest style Zydeco Kitchen & Cocktails, Middle-Eastern fare at Joolz or cuisine served with European flair at 900 Wall. Don’t miss the giant pastries at Sparrow Bakery. Just across the street, find eco-friendly gifts at The Workhouse, a newish space that features the work of local crafters and hosts drop-in art-focused events.

It’s always five o’clock somewhere, so take your Bend Ale Trail interactive map to more than a dozen Bend low-key breweries for an IPA and a bite if you’re so inclined. Bridge 99 Brewery, Monkless Belgian Ales and GoodLife Brewing Co. and the granddaddy of them all, Deschutes Brewery, are all fantastic bets. (Craft beer lovers may want to plan a trip around the High Gravity Brewfest).

Ice sculpting at Oregon WinterFest by Brian Becker

3. Mountain culture heats up: Arts, theater, song and dance  

On your day off from the slopes, know that downtown Bend is a flurry of eggnog-fueled festivity. Pop in for live jazz at the Oxford Hotel weekly between October and March. Enjoy local talent from community theater at Cascades Theatrical Company, which lights up the stage with shows throughout the winter. Keep the party going with a celebration of songs, dances and stories at The Tower Theatre. But wait, there’s more. Tin Pan Theater, tucked away in a downtown alley, also shows independent, foreign and documentary movies in an intimate setting, and 2nd Street Theater in Bend’s burgeoning Maker’s District, has a great slate of shows on tap.

Whether under snow or clear skies, put on your dancing shoes (aka winter boots) and cut a rug at the free Apres Ski Bash. The free outdoor concert series at Crow’s Feet Commons, downtown, features boot-stomping bands one Friday per month through April. In mid-February, the Old Mill District transforms into a festive winter wonderland, as Oregon WinterFest during Presidents’ Day weekend features live music, a skiing and snowboarding rail jam, obstacle course, 5K run, and play areas for the family. Enjoy a snack under the buzzy glow of the lighted art pieces along the river, or stay warm by the firepit while you watch chainsaw-wielding ice sculptors in competition.

Courtesy of Mountain Air Trampoline Park

4. The family plan

Yes, Bend is Beervana but it’s also a family-friendly mecca, especially in the winter. You can all escape the chill and warm up with a restorative visit to the soaking pool at McMenamins Old St. Francis School, where the treasure hunters in the family will have a blast looking for the secret rooms on the property. Cuddle up on a couch at the brewpub’s cozy theater, where mom and dad can enjoy beer or wine and and littles will be thrilled for pizza.

 Share your love of art with the kids at Bend’s diverse array of local galleries, including the Mockingbird Gallery in downtown Bend; the Tumalo Art Co. in the Old Mill District; or the Bend Art Center in the historic Box Factory, where you can create your own art. Just 10 minutes south of town, make time for a trip to the High Desert Museum for their latest exhibit, such as the beautiful “Things You Know But Cannot Explain,” which memorializes the work of the late Oregon indigenous artist Rick Bartow. If the weather is keeping you inside, book a jump time at Mountain Air Trampoline Park for some seriously sweaty fun; Friday and Saturday nights the whole family can enjoy cosmic jumping with party lights, fog machines and glow-in-the dark dodgeball and basketballs.

Want to skip driving for a while? Bend’s compact downtown makes it easy to walk everywhere. Explore the Pile the family into an e-cruiser for a highly entertaining narrated tour of the city’s public art and cultural landmarks — just one of many guided experiences offered by the Bend Tour Company. If you go on your own, make it a treasure hunt — pick up a map of the Roundabout Art Route’s more than 45 sculptures around town and let the kids guide you; bring your completed quiz to the Bend Visitor Center for a souvenir. There’s still more gorgeous works to see at the Tin Pan Alley Art Collection and Pillars of Art.

Courtesy of Mt. Bachelor

5. Savor the snowflakes: Sled, snowshoe, dog sled, ice skate, fat bike on the snow

You can’t beat a bluebird day at the mountain, and Mt. Bachelor has plenty to offer beyond downhill skiing and snowboarding. Take a break from the lifts and try something new, like riding with a guided sled dog team. If a need for speed is in order, try Mt. Bachelor’s Snowblast Tubing Park, where a specially designed tow makes it easy to go again and again. Or make first tracks across the quiet winter terrain on a pair of snowshoes. Trails take you through the forest starting at trailheads such as Swampy Lakes and Virginia Meissner sno-parks, and often permits are required. Find guided snowshoe tours through Mt. Bachelor (with a U.S. Forest Service naturalist, free) and Wanderlust Tours. Rent snowshoes or sleds at REI and Bend Tour Company.

Bike nerds need not feel left out. At Wanoga Sno-Park, you’ll find groomed trails perfect for fat biking in the packed snow — similar to dirt biking, but a bit more fun due to the slipperiness. Rent a bike at any of several local outfitters; gear up properly and and read up on tips before you go. Maybe a special occasion calls for a splurge — in that case, take in the Central Oregon’s landscape from a spectacular aerial view with a helicopter tour of the mountains with Big Mountain Heli Tours.


When you go:

Make sure to visit Bend’s Visit Like a Local page and learn how to leave the place better than you found it — by packing out trash, staying on trails, preparing for shifts in weather and even random episodes of magic. Sign up for the Bend Pledge for a chance to win prizes, including a trip to Bend. Find great deals on lodging — from cozy and rustic to plush and deluxe — and check out more Bend trip ideas for inspiration.


Trip Ideas