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Winter Destination: Bend, Oregon

Winter Destination: Bend, Oregon

Only go to Bend, Oregon in the winter if you love relatively short lift lines, epic views from the chair lift, and frequent bouts of fresh powder. Go if you love snowshoeing on pristine Nordic trails in the moonlight. And definitely go if you love really great après-ski food and drink.   

Don’t get me wrong: Bend is also amazing in the summer (in fact, I actually prefer summers in Bend to just about anywhere else on earth), but we’re talking about the particular delights of winter here — and those are many.

Bend is smack dab in the middle of Oregon, making it three hours from Portland and three hours from the ocean. It is surrounded by thousands of acres of high desert on one side, and the Cascade Mountains on the other. The majestic Deschutes River runs through it, along with miles of trails that are perfect for day hikes, dog walks, and general meandering.

In the past decade, tens of thousands of new residents have descended upon Bend to escape the travails of city life, transforming it from a sleepy, small, resort town to a bustling, almost-city of 90,000. As a result, there is now a restaurant and coffee scene that will placate even a medium-picky Portlander. There is also a very respectable arts and music scene, and a talented community of healers and yogis.

Despite its sophistication, however, Bend has managed to retain plenty of its ski bum roots. You don’t have to go far to get a locally brewed beer or hit up a food truck, and the local values center strongly around community and quality of life over “progress.”

One caveat about your trip to Bend: you will most likely leave with a hankering to move there. Just remember that even if relocation is not currently in your cards, it makes for one heck of a happy place, where you can always go for a visit and will never be disappointed.


  • - Some of the best Bend lodging can be found on Airbnb. You can also find a variety of lodging options at McMenamins St. Francis School. I love its rustic decor, awesome movie theater, Irish pub with indoor and outdoor fireplaces, and famous Turkish-tiled soaking pool
  • - Cross-country skiing up to Tumalo Falls is a gorgeous winter excursion. Those who are moderately fit can do this gradual, uphill climb comfortably, and the super fit will love it too
  • - Check out the 2,500 acres of skiable terrain at Mt. Bachelor. If you get there for the first run of the day, you will likely catch the colors of an amazing sunrise on the Sisters mountains
  • Joolz for dinner – try the Cauliflower appetizer and the Seafood Tagine for your main course!
  • El Sancho for après-ski tacos. There’s a line out the door every day, and you’ll see why once you eat there
  • - Try Brother Jon’s Public House for great comfort food in an atmosphere that is equally comforting and warm
  • - Get your juice and smoothie fix at Mother’s Juice Café. They also do great sandwiches and soups
  • - To get to and fro, fly into the Redmond Municipal Airport. It’s definitely one of the most charming airports you’ll visit and makes travel to this relatively remote location easy and quick


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