Your winter weekend itinerary for a family vacation in Bend, Oregon
I hosted a houseful of out-of-town relatives over Christmas, an endeavor that left my living room looking like someone detonated an explosive filled with pine needles, giftwrap, and empty beer growlers.
But one upside to hosting guests who visit Bend once a year is the opportunity to experience the town through the eyes of a tourist.
Comes in handy when you work in tourism.
If you’re looking for a Bend winter vacation itinerary to entertain family members ranging from 5 to 65, here’s what I suggest.
Day one: hiking and sledding and eating, oh my!
Round up the early risers and go for a morning walk. There’s nothing quite like watching the sun rise in Bend, whether you’re strolling along the Deschutes River near the Old Mill District with a cup of coffee in hand, or taking Fido to the 18-acre Bob Wenger Memorial Off-Leash Area in northeast Bend. The sun rises late this time of year, so bring a headlamp if you need to, and make sure you’re bundled up nice and toasty warm.
Time for breakfast! You’re headed up to Mt. Bachelor today, so nudge the late sleepers awake and grab something quick you can eat in the car. Check my post on 9 spots for a grab-and-go breakfast in Bend if you need ideas.
The best thing about Mt. Bachelor is that there’s something for everyone. The ski bums and snowboarders will love shredding 3,700 acres of lift-accessible terrain with the highest skiable elevation in Oregon and Washington. Non-skiers will appreciate activities like snowshoeing, sled dog rides, and my family’s personal fave, the Snowblast Tubing Park. Be sure to check Mt. Bachelor’s website for hours and condition reports before you head up.
If you opted for a two-hour session in the tubing park, you should be back in Bend by lunchtime. Reward yourself with a stop at Longboard Louie’s, where you’ll find options for everyone from picky kids to vegans and gluten-free diners. (Pro-tip: Ask for the Recession Buster Burrito. It’s not on the menu, but it’s a basic bean and cheese number you can trick out to make it the perfect lunch. Have ‘em toss in some meat, fajita veggies, and guac, then hit the salsa bar for a delicious all-in-one meal for under $6).
With bellies full and fingers still a bit chilled from your morning on the mountain, it’s a good time for something indoorsy. Sun Mountain Fun Center is a fun option with kids in tow, or try the High Desert Museum for a good mix of education and critter love. For something active and super unique, head to Peak Airsoft for some family warfare at their indoor arena, or see if you can solve your way out of Bend Escape Room.
By now, you’ll have a few members of the family feeling tuckered out, so grab takeout from Cibelli’s Pizza and head back to your Bend vacation home or hotel for an evening of games or soaking in the hot tub.
Got a few family members who aren’t ready to call it a night? Leave the grandparents in charge of the young’uns and head out on the town for an evening cocktail. Try Dogwood Cocktail Cabin if you’re looking for some of the most unique concoctions in Bend, or if you’re craving a late-night happy hour, hit 10 Below or The Blacksmith to wind down your day in style.
Day two: more food, more snow play, and beer!
After the hustle and bustle of your first day, you’re due for a more leisurely breakfast. Check out my post on 6 spots for Bend’s best eggs benedict. Then get ready to lick the plate clean.
Now you’re ready to hike off a few of those extra calories. The Oregon Badlands Wilderness is one of my favorite spots this time of year to explore craggy lava flows and ancient junipers. If you prefer a snowier scene, strap on the snowshoes and sashay out to Tumalo Falls. Winter road closures mean you’ll need to park at the gate and hoof it 2.5 miles each way, but it’s well worth the trip.
Lunchtime? If your family is like mine, you’ve got a crazy mix of dietary needs ranging from carnivore to vegetarian to allergies that can make dining out a little scary. Simplify things by checking out this blog post featuring 10 vegan dishes you’ll love even if you’re a meat-eater (I promise!) or this post offering 7 gluten-free eats you should devour even if you’re not gluten-free. Of course, if you’re a family of carnivores, you can also reference this post on Bend’s best burgers or this one on Bend’s best hot wings.
Feeling full? Time for more exercise! If you’re craving another round of snow play, leave the driving, gear-wrangling, and decision-making to Wanderlust Tours when you book a family snowshoe adventure with them. Not so keen on the white stuff? No problem! Opt for a snow-free outing with one of their lava cave tours instead.
If the Bend Ale Trail is on your wish list, don’t feel like you have to miss it just because you have little ones in tow. Bend Brewing Company and Deschutes Brewery both boast excellent kids’ menus, scrumptious grownup offerings, and beer taster trays that will give your family a chance to sample a variety of styles and flavors.
If you’re feeling fancy for dinner, cap off your vacation with a meal at one of Bend’s best dining establishments. Among those I routinely recommend to foodie journalists: 5 Fusion, Zydeco, Jackalope Grill, Ariana Restaurant, and Trattoria Sbandati. Relative newcomer Fire in Bend has a kids-eat-free deal on Sundays, so head there if your party includes a few members 13 or younger.
Cap off your night with a soak in the glorious turquoise-tiled saltwater pool at McMenamins Old St. Francis School. Study the stars though the open-air ceiling, and admire the luminous stained glass and hand-painted artwork. Ahh . . . this is living!
Planning a trip to Bend? Check out our award-winning visitor guide online, or request one to be mailed to you.Read the Guide
Give Us A Call
Want to talk to a real human? We get you. Our visitor information specialists are here to take your call Monday - Friday, 9:00 a.m. - 5:00 p.m. and weekends, 10:00 a.m - 4:00 p.m.Call : 877.245.8484
Stay In Touch
Want to keep up with all of the latest and greatest happening in Bend? Sign up to receive our email newsletter. We promise not to spam you, and we'll respect the heck out of your privacy.
Join thousands of other Bend visitors and take the Pledge to leave Bend better than you found it. Bonus - you can sign up to win a vacation to Bend, too.Take The Pledge