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3 winter itineraries for Bend, Oregon      

A group on a snowshoe trek near Bend, Oregon.

Folks start searching the interwebz for “Bend winter vacation” long before the season’s first snowflakes fall. By November, everyone’s frothing with fervor to ski, sled, or stroll among the frost-speckled trees.

Whether you plan to spend each waking hour at Mt. Bachelor or you’re scanning our weather page to avoid the white stuff, we’ve got the perfect itinerary to plan your best winter trip to Bend.

Aerial photo of the snowfall in Bend, Oregon.

November in Bend is the perfect time to see the lingering colors of fall and the first flakes of snow mix in the landscape.

Let it snow, let it snow, let it snow!

If you’re visiting Bend from someplace that doesn’t see much snowfall, you’re likely seeking a snowflake fix. 

Start your snow-venture on your very first evening with a moonlight snowshoe outing with Wanderlust Tours. They’ll provide all the gear, transportation, and snacks as your skilled naturalist guide leads you to a magical amphitheater hand carved in snow. There, you’ll enjoy a warm drink and a starlit bonfire. Don’t worry if you’re not a night owl––Wanderlust does daytime snowshoe trips, too.

For lodging, pick a spot along Century Drive so you’ve got a straight shot to Mt. Bachelor on your first morning in town. Pine Ridge Inn, LOGE Camp, and Mt. Bachelor Village Resort make excellent options with their own spin on the cozy, ski village vibe you’re seeking.

Aerial view of over 4,300 acres of skiable terrain at Mt. Bachelor in Bend, Oregon.

Early season snow coverage at Mt. Bachelor. Photo courtesy of Mt. Bachelor / Austin White.

With a good night’s sleep under your belt, it’s time to hit the slopes! Head for Mt. Bachelor to find a winter wonderland of skiing, snowboarding, dog sled tours, Nordic skiing, and more. If you’ve got kiddos in tow, you’ll love their Kids Ski Free program, while newbies of all ages can jumpstart their skills with Ski or Ride in 5.

If you’ve still got gas in the tank after a day of snow play, peruse our roundup of Sno-Parks where you can try sledding, try cross-country skiing, or take a fat bike out for a spin on snowy trails. For a change of pace that still involves frozen water, take a twirl on the ice at The Pavilion.

Still don’t have your fill of skiing? Head for Hoodoo Ski Area and embrace 800 miles of terrain, 34 runs, five lifts, and one of the largest tubing parks in the west. They even offer night skiing to fill your round-the-clock snowplay needs.

Can I skip the snow, please?

If you picture Bend blanketed in white from November through April, the truth is that the city itself gets less fluffy stuff  than you’d think. The average Bend snowfall is 33.8 inches, versus an average of 160-180-inches at Mt. Bachelor just 22 miles up the hill.

What that means is that it’s fairly easy to avoid walking in a winterland if that’s not your scene. 

Group of women trying on winter accessories during a shopping trek in downtown Bend, Oregon.

Take a break from the snow play and stroll the shops in downtown Bend.

Instead, focus on an urban Bend adventure. Park yourself in the heart of the city with a room at the Oxford Hotel or Wall Street Suites, or the Element Hotel.

From your Downtown digs, you’ll have an easy time walking to Bend’s best happy hours at hotspots like Dogwood Cocktail Cabin, Stihl Whiskey Bar, or San Simon. For a glimpse at an itinerary for the ultimate Bend cocktail crawl, check out this post.

When your belly starts growling, it’s time for dinner. Like most towns these days, Bend took a hit from the pandemic, and staffing shortages mean reservations may be required––even during slow winter months.

A few spots worth adding to your bucket list include Yoli for tasty Korean fare, Bos Taurus or Brickhouse for scrumptious steaks, 900 Wall for yummy modern American cuisine in a cool space, or Chomp Chomp for mouthwatering Japanese American meals. 

If you’re venturing past the downtown core, don’t miss Bosa for outstanding Italian eats, Greg’s Grill for divine dining with a river view, or Rancher Butcher Chef for farm-to-table fare. Vinophiles will want to head straight for Flights to score unique wine flights and creative cuisine to match.

Not ready to call it a night? Cap of your evening with a wine flight at the Domaine Serene Wine Lounge and don’t forget to slip downstairs for a glimpse at their historic speakeasy. You can also catch the late-night happy hour at Blacksmith where you’ll get another dose of Bend’s unique history in this quirky-cool former blacksmith shop.

Feeling more of a beer vibe? Some of the Bend Ale Trail’s most popular stops sit right in Downtown Bend, including Bend Brewing Company, Deschutes Brewery, Silver Moon, McMenamins, and even tasting rooms for Redmond-based Kobald Brewing and Porter Brewing. Bring your Bend Ale Trail passport or app and check a few boxes to earn prizes for sipping your way around the territory.

Sprinkle some culture into your Bend adventure by catching a show at the historic Tower Theatre. You can take in the Roundabout Art Route all on your own, or stroll through countless art galleries. For more ideas, check Visit Bend’s event calendar to see what’s happening during dates you plan to play in Bend.

Frost covered Old Mill District In Bend, Oregon.

The Old Mill District is the perfect mix of shopping, dining, and the outdoors in one place.

While Downtown Bend offers an endless bounty of shopping, expand your horizons by strolling the Box Factory, which is packed with fun shops and amazing eateries. Continue your exploration of Bend’s prime shopping districts with a jaunt into the Old Mill District and a chance to stroll alongside the stunning Deschutes River with a warm mug of cocoa in hand.

Want to squeeze in a hike? This blog post rounds up some of Bend’s most inspiring winter hikes where snow’s less likely to be a factor. Happy exploring!

Hit the road with Rover

Want the ultimate dog-friendly winter vacation in Bend? Start by perusing this page for pet-friendly lodging. The Riverhouse boasts easy access to the river trail for prime dog walking, or give your pooch a pinch of luxury at The Oxford Hotel. You can also scope out the boutique camping and RV experience at The Camp, whether you’re pulling your own trailer or rent one of theirs.

Now that you’ve got your dog-friendly digs, it’s time to explore. The folks at DogPac offer an awesome roundup of dog-friendly trails for both winter and summer. I’m a big fan of the Oregon Badlands Wilderness for its acres and acres of off-leash exploration. Be sure to bring extra water, since it’s a dry desert out there.

Coupld walks with their dog at Dry River Canyon near Bend, Oregon.

Make sure your pup enjoys some snow play while you’re in Bend!

For pups who do best when contained, Bend boasts a whopping eight (yep, EIGHT!) off-leash dog parks. My personal fave is the fully-fenced 18.8 acre Bob Wenger Memorial Off-Leash Area on the northeast end of town. From trails to grassy fetching areas, your pooch will find plenty to wag about.

With all that outdoor frolicking, Fido’s getting stinky. Swing by Bend Pet Express to hit the U-Wash dog station, or leave the sudsing to their talented groomers while you browse for dog snacks and toys. In Downtown Bend, stop by locally-owned Bendy Dog for everything from dog jackets to treats. You can also grab dog booties if you need ‘em before hitting Bend’s snowshoe trails––especially the dog-friendly ones I spotlighted in this post.

Need time apart from your pup so you can try some of Bend’s dog-free offerings? You’ll find oodles of great pet sitters, doggy daycares, and even a dog hotel in Bend.

Couple enjoying a beer by the fire at Bevel in Bend, Oregon.

After your hike, enjoy a beer by the fire at Bevel Craft Brewing.

Cap off your dog-friendly winter vacay with dinner out for the two of you. Perhaps a fireside spot on the cozy, dog-friendly patios at McMenamins, Bevel Craft Brewing, GoodLife, or Worthy Brewing. Both Worthy and Sunriver Brewing even offer special menu items just for dogs, so Fido will truly feel like part of the pack.

While you’ll want to leave Rover behind for a fine dining date night, he’ll know you’re thinking of him if you eat at Zydeco. They bake fresh dog treats daily to please your pup’s palate, so ask for some when you get your doggie bag to go.

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