72 Hours of Winter in Bend: Your Itinerary Awaits

We always encourage play in Central Oregon, and winter is no exception. Luckily in Bend, blankets of snow are plentiful. When the holidays slow you down and the weather keeps you humble, here’s what to see, do, and eat on your quick trip to Bend (good luck not extending your trip!)

Now, 72 hours is not nearly enough time to get a sense of all that Bend offers. And there’s a LOT. From premier coffee shops for chatting, bars to sip hot toddies, breweries for apres burgers, and downtown activities that will make you swoon, we’ll do our best to narrow it down. Get your planners and winter boots ready.

DAY 1: Gear Prep & See the Sights

A group of snowshoers at Wanderlust Tours.

First day in Bend. Lucky you! You’ll want coffee & breakfast stat, so we won’t delay. 

On your way to an activity and want something quick? Head to Sparrow Bakery for an infamous ocean roll or one of their addicting breakfast sandwiches. If you’re planning to sleep in or just want to relax, go to Chow or Lemon Tree for fresh, local ingredients, a varied menu, and good vibes. 


Now, let’s grab your gear. With so many adventures here, the demand for rental equipment is big, and the options are plentiful. Luckily, ski rentals in Bend provide it all: from cross-country to downhill and backcountry touring.

Head over to a gear rental spot around town, like Powderhouse or Skjersaa’s Ski & Snowboard shop. They’ll have top-of-the-line equipment AND show you how to use it. They may even offer their top trail maps, tips, and fave spots to see! Win/win.


If you’re looking for a more easygoing experience, grab a pair of snowshoes to experience winter in the most peaceful way possible. Or, take a hike and explore one of the many spectacular SnoParks along Cascade Lake Highway, like Swampy Lakes Sno-park

Don’t want to go at it alone? Wanderlust Tours provides all the fun you’ll need with a planned-out itinerary around Mt. Bachelor and the forests of the Cascade Mountain Range for day or night (moonlight snowshoe, anyone?) Hot cocoa included! If you want more of an inside scoop, check out our page for all things snowshoeing in Central Oregon.


You’ll be tuckered out after your day outside. For lodging, if you’d like easy access to Mt. Bachelor in the morning, try to grab a spot along Century Drive at LOGE Camps, Mt. Bachelor Village Resort, or Tetherow Resort just 20 minutes from Mt. Bachelor and downtown Bend.


You’ve likely driven by the Box Factory on your way to town. It’s filled with cool shops like Danner and offers endless options to chill with a cold one (think: cider at Avid, beer fireside at Crosscut Warming Hut, or cocktails at Brown Owl). For the post-dinner nightcap, check out at Bledsoe Family Winery. If it’s earlier in the day and you need a pick-me-up, head into Spoken Moto for espresso and continue your exploration of Bend with a gander over to the Old Mill District. Bonus points for grabbing hot cocoa at the new Sisters Coffee for a stroll along the river before eating at Greg’s Grill or Pastini’s. 

DAY 2: Snow Sports A-Plenty

Do you hear that? That’s the sound of the snowy peaks calling your name. Time to grab your planks, boards, warm bevies, and a quick brunch from Jackson’s Corner to head out for some winter fun.

A person ski jumps at Mt. Bachelor


Set your sights on Mt. Bachelor to find your dose of a winter wonderland. You’re about to discover one of the PNW’s best in skiing, snowboarding, dog sled tours (yes, really!), Nordic skiing, and so much more. If you’ve got the tykes in tow, check out the Kids Ski Free program. Been a while? Jumpstart your skills with Ski or Ride in 5. However you slide, make it a season to remember in Bend. 


If you’re not planning on kicking it at the mountain but you still want your fix, get your skinny skis on and check out the incredible SnoParks close to town off Century Drive on the way up to Mt. Bachelor. The most popular is Virginia Meissner for Nordic skiing enthusiasts, which stays afloat on donations. If you have your pup along, bring them along to the dog-friendly groomed trail at Wanoga Sno-park. The best part is, you can bring snacks and take a time out in the many warming huts with fireplaces throughout the trail network!

Ungroomed trails are also an option if you prefer stomping over sliding. Check out more dog-friendly trails Kapka Butte Sno-Park. No matter if you’re skiing, sledding, snowshoeing, or just plain playing in the snow, you’re in for a grand old time. If you haven’t had your fill of fluffy snow yet, head for Hoodoo Ski Area and embrace the legendary night skiing and miles upon miles of terrain. 


While you’re riding that adrenaline high, venture to one of 30 breweries in town, like Deschutes Brewing, Sunriver Brewing, Crux, or Bend Brewing Co for post-mountain fun and food. 

DAY 3: Urban Exploration Time

A plate of food at Bosa.

Ah, Bend. What a magical place for a downtown hang. Get ready for some of the best strolling around. First, if you want to stay closer to town, shlep your stuff to the heart of the city at The Oxford HotelWall Street Suites, or the latest Element Hotel.

Peek over to the historic Tower Theatre, and take a gander at the holiday-decorated downtown streets for all the shopping, live music, and art galleries. Check out Visit Central Oregon’s event calendar on the exact days you’ll be around.


From your digs, walk to happy hour at Dogwood Cocktail Cabin or San Simon for the best hot toddies in all the land and build-your-own charcuterie boards. For more on the hottest spots for sipping during your stay, check here.


Ready to nosh? Add these tasty bites to your bucket list ASAP. If you’re feeling sushi, make a reservation at Five Fusion. For steaks, you’ll want to grab a spot at Brickhouse or 900 Wall for tasty modern fare and prime locations. 

If you’ve ventured past the core of downtown, don’t miss Bosa for Italian eats (check for reservations!), the Lot for elevated food truck fare like fish tacos, or Sen Thai for a yummy hot pot to warm you up after a day on the slopes.

Cap off your evening with a spot of locally made gelato at Bonta, or a wine flight at the Domaine Serene Wine Lounge.

Got a bit of extra time? Peek these hints for your winter fun in Bend.

For the winter-hiking fanatic 

Wanna squeeze in a hike? You’re likely to get them all to yourself! Here are some spots where snow is unlikely to be a huge factor. 

Fireside dog-friendly bar patios 

Seek a fireside hang at Worthy Brewing, McMenamins, Bevel Craft Brewing, Bend Brewing Co, or Goodlife. (Fun fact: Sunriver Brewing even offers menu items for dogs!)

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