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Bend, Oregon

"AMERICA'S BEST MULTISPORT TOWN" Outside Magazine

Hailed as one of the best towns in the country by residents and visitors—oh yeah, and reputable sources such as Outside Magazine—Bend is an outdoor enthusiast hub with a bit of urban cool.

 

The Tower Theater in Downtown Bend, Oregon
The Tower Theater in Downtown Bend, Oregon

Touting titles like BeerTown and DogTown USA, Bend is one of those places that’s tough to leave once you’ve arrived. Frequently gracing “must-travel” lists, this mountain town with impressive views of the Cascade Range, 30+ craft breweries, 63 miles of urban trails including the Deschutes River Trail, 300 miles of single-track trails and more than 80 parks and open spaces delivers a memorable experience for the whole family. Access to alpine lakes and Mt. Bachelor – the country’s 6th largest ski area -, which is open for all-season fun, including downhill mountain biking is just a short drive up the Cascade Lakes Scenic Byway. Complementing the wide variety of recreational opportunities, upscale restaurants, and luxury accommodations, from boutique hotels to destination resorts, ensure Bend is a place worthy of your vacation.

SAMPLE WINTER ITINERARY:

Bend knows how to show off winter to its visitors. 

When skiers, snowboarders and those just looking for a winter getaway come to town, Bend delights with plenty of opportunities to get out in the cold and marvel at the mountains. Or, stay cozy indoors with a winter beer and some of Bend’s best comfort foods. 

Start your day at one of Sparrow Bakery’s two locations — if Bend had an official city pastry, it would be the flaky, cardamom-infused Ocean Roll. If you’re looking for a place to settle in for a big brunch, try Lemon Tree or Brother Jon’s Alehouse — both downtown, and both serving up breakfasts that will please any palette.  

Time to work off some of that decadent breakfast? Winter in Bend offers no shortage of options for a workout. Stay close to home with a wintry walk through Drake Park, Bend’s photogenic and historic spot right on Mirror Pond. Follow the river upstream and you’ll find yourself at the Bend Whitewater Park, which often has surfers testing their skill no matter the weather. 

Rent a fat bike from Pine Mountain Sports or Hutch’s, then explore on two wheels — the large, tread-heavy tires will give you plenty of traction on snow and make more locations accessible. Or check out Wanderlust Tours, which organizes daily winter outings that range from snowshoe tours and bonfires to snow camping and cave tours. 

Then, of course, there’s the juggernaut of the region — Mt. Bachelor, which has the most skiable terrain in Oregon and among the most in the United States. Seven high-speed lifts, tons of snow and smaller crowds than other ski resorts around the Northwest. In a lot of ways, the mountain feels like an extension of Bend itself — small-town feel, outsized fun. 

If vertical runs aren’t your thing, Mt. Bachelor also has a Nordic Center with lots of terrain for cross-country skiing. 

Should you find yourself in Bend for Oregon Winterfest, February 14-16, make it a priority. The three-day festival has live music, the Light, Ice & Fire Exposition, which features fire pits, ice sculptures and light art, and the ever-popular rail jam, with skiers and snowboarders showing off their trick skills. 

For those not interested in braving the winter chill, check the schedule at the Tower Theatre, which serves as the living room of Bend and often has top-name acts in town. Another great option is the Deschutes Historical Museum, which has both permanent and rotating exhibits that explore Bend and Deschutes County’s vibrant past. 

After all that adventure, you’ve earned a beer or two. Bend has more than two dozen breweries, and it’s not a trip to Bend unless you visit a few. You can access the Bend Ale Trail on your own, or hire a tour group such as The Bend Tour Company or the Bend Brew Bus to give you a lift. Locals will thank you, since IPAs can be high in ABV and our city is at about 3,500 feet. 

Finish your day with a meal from one of Bend’s great restaurants. No matter what type of fare you seek, Galveston Avenue has you covered. If you seek fine dining, try Ariana, which has a daily five-course chef’s menu that is creative and compelling. 10 Barrel Brewing’s westside pub down the street is the right spot for pizza and comfort food. And locals love Parrilla Grill, a small, low-key place with inventive burritos and excellent fish tacos.  

At the end of your long, busy day, try the quirky McMenamins Old St. Francis School, which has bars, restaurants and soaking pools (perfect after skiing) on the property. Or get some sleep at the Hampton Inn & Suites right in the heart of the Old Mill, so you don’t miss a thing. 

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