I met my stepkids when they were 5 and 9. Our get-to-know-yous took place gradually along hiking trails by the Deschutes River and giggling snowball fights in the park.
Here’s the thing about kids: They don’t stay young. That 9-year-old is now 18, and how the heck did I get a middle schooler?
But the nice thing about Bend, Oregon is its magical way of unleashing everyone’s inner child. With the clock ticking on Kid 1’s college departure, we set out to enjoy one last winter vacation in Bend.
Our mission: Blending the best of childhood nostalgia with activities even the moodiest teen will love. Here’s how it all went down.
No matter how big they get, kids go nuts for swimming pools. That’s why we love The Riverhouse and its indoor and outdoor pools and hot tubs. It’s great for all seasons, plus their variety of room configurations gives us a touch of privacy and separate beds.
Having older kiddos offers more freedom for a grownups-only happy hour at Currents while the teenagers grab a workout in the fitness center or take the dog for a walk along the Deschutes River.
And the whole family digs their dinner menu that ranges from flatbreads and fries, to filet mignon and escargot.
We’ve hiked Pilot Butte as a family dozens of times, and you know what? It never gets old.
When the kids were little, we’d take a bottle of bubbles and let them chase the shimmering orbs at the top of cinder cone. These days, they’re more interested in charcoal sketching the scenery or snapping selfies against the mountain backdrop. Either way, the 360-degree views from the top are a great way to get oriented to Bend’s layout. It’s roughly 30 minutes to the top, and a lifetime of bragging rights for hiking a dormant volcano.
Back at the bottom, we head for our post-hike reward of burgers and shakes at Pilot Butte Drive-In.
Fueled by a hearty lunch, we make a beeline for the High Desert Museum to hit their afternoon Birds of Prey Encounter. If we’re extra lucky, we might catch an Otter Encounter when the adorable little river kitties are out clamoring for fish.
Animals aside, there’s plenty to entertain kiddos at this high desert oasis. Littles love the Spirit of the West tour and a chance to scope out a silver mine or see what a fur trader camp looked like. My art-minded teen adores the Native American bead exhibits, while the younger is intent on scoring a fresh-baked cookie in the café.
Afterward, we reminisce about the animals we saw and engage in a rousing family debate about whether a porcupine or an eagle would win in a street fight.
You don’t need to skip the Bend Ale Trail just because you’ve got minors in tow. My science-obsessed kiddo loves the factory tour at Deschutes Brewery, including samples of housemade root beer and a lesson on the fermentation process.
For a sit-down-and-eat experience, we hit Crux Fermentation Project and load up on Grilled Cheesy sandwiches all around. Bonus: There’s a big, grassy field for getting the wiggles out. Bend Brewing Company also boasts an outdoor area, with extra points for an awesome kids’ menu.
At the end of an evening, nothing beats family snuggle time by a fire pit at Worthy Brewing, capped off by some stargazing through the telescope in their Hopservatory.
Bend in wintertime means snow play, and Mt. Bachelor has it in spades. We hit Sparrow Bakery on the way for their famous Ocean Rolls and grab-and-go breakfast sandwiches.
Arriving at the mountain, we get everyone squared away with lessons and rental gear. We’re past the age of qualifying for Bachelor’s Kids Ski Free program, but it’s a killer deal for families on a budget with kiddos 12 and under. The promo is only available Nov. 25-Dec. 15 online, so it pays to plan ahead.
If attention spans wane, we head for the Snowblast Tubing Park for an hour of zipping down the slopes in plump inner tubes. You know those teeth-grinding moments when your offspring whine for help hauling their sleds up the slope? That’s not a thing here, where a tow rope keeps everything flowing nice and easy.
We’re off the mountain, and it’s time to fill the tanks for our next adventure. A stroll through the Old Mill District lands us at Flatbread Neapolitan Pizzeria where kids are supplied with dough, sauce, cheese, and toppings to make their own pizzas. While their father and I sip cocktails and share an appetizer, young’uns watch their creations cook up in the big wood-fired oven.
Fueled for adventure, it’s time to head out with Wanderlust Tours for their moonlight snowshoe tour. Their naturalist guides make it fun to learn about local wildlife and geology, and everyone’s rewarded by the bonfire in an amphitheater hand-carved in the snow.
If early bedtimes make a night tour impractical, don’t worry! Wanderlust offers daytime adventures, including snowshoeing and cave tours. They provide gear, transportation, and guiding, so all you have to do is kick back and enjoy this special brand of family bonding.
Everyone’s tuckered from yesterday’s snow play, so today’s an indoorsy kinda day. We start with breakfast at Jackson’s Corner on Bend’s quieter Eastside, filling up on French toast and their scrumptious biscuits and gravy.
Then we’re off to Trampoline Zone to bounce ourselves silly (Moms: Pack a sports bra. You’ll thank me). Warmed up and giggled out, we head for K1 Speed and my futile attempt to beat my children in an indoor go-kart race. #Someday
Lunch at little tucked-away Craft Kitchen and Brewery fills our bellies with mouthwatering barbecue and some house mac and cheese for the kids. Then we’re off to Sun Mountain Fun Center for a family bowling challenge and an afternoon of arcade play.
Congratulations, family. We’ve done the ever lovin’ heck out of winter in Bend, Oregon.
Want to know the upside of living and playing in Bend, Oregon for 22 years?
Okay, technically, there are 2,986,321 upsides (give or take 13).
Chief among them is that when pals come to town looking for The Very Best Winter Weekend in Bend™, I know just what to tell them. Here’s how it’s going down.
My friends roll into town and settle into their deluxe rooms at The Oxford Hotel. It’s a handy spot for strolling the shops and restaurants of historic Downtown Bend, plus the upscale boutique vibe is a chance to treat yo’ self (seriously, check out the pillow menu).
We drop the bags, lace up the hiking boots, and prepare to play. Pilot Butte is a good starting point for its location smack-dab in the middle of the city, plus we get cool points for hiking an extinct volcano. It’s roughly 30 minutes to the top for 360-degree views of the whole city, plus mountains and desert beyond.
After hoofing it down, we reward ourselves with juicy burgers at the iconic Pilot Butte Drive-In.
Overachievers that we are, we’ve pre-burned our beer calories by hiking. Time to hit the Bend Ale Trail!
From a home base in Downtown Bend, we’re easy walking distance to primo spots. Want a quieter, locals’ hangout vibe with great beer, a riverfront location, and tasty food? We’ll pick Bend Brewing Company. Want to pay homage to the granddaddy of Bend’s beer scene with bustling energy, killer tap lists, and an expansive menu? Hello, Deschutes Brewery. Feel like capping off dinner and beer with a soak under the stars, a cozy sofa in a movie theater, or even a cigar bar? Here we come, McMenamins Old Saint Francis.
If we’re feeling snacky after, we’ll hit the late-night happy hours at 10 Below or Blacksmith, which offer close proximity to the cushy hotel pillow that’s calling our name.
We’re up and at ‘em early the next morning for a day of winter play at Mt. Bachelor. To keep it simple, we swing by Mother’s right outside the hotel for tasty grab-n-go breakfast sandwiches and smoothies.
Once we hit the mountain, it’s tough to choose just one form of snow play. Fans of skiing and snowboarding can head right for the slopes to enjoy more than 4,300 acres of lift-accessible terrain. Newbies with an urge to learn will find easy access to discount lessons and rental gear. We can even try our hand at Nordic skiing, since Bachelor boasts 56-kilometers of machine groomed track and North America’s longest groomed Nordic season.
There’s always someone who’d rather not strap boards to their feet, so I point them to the Snowblast Tubing Park. It’s like the sledding hill you remember as a kid, but with deluxe inner tubes and a tow rope to ensure you don’t have to drag that bad boy up the hill yourself.
Afterward, let’s meet at Mt. Bachelor’s Clearing Rock Bar for cocktails and Bachelor’s famous Nacho Mountain.
My pals have come to Bend for the ultimate in winter play, so we’ll serve up a second helping. After a quick dinner of handmade pastas, pizza, pasta, and farm fresh salads at Jackson’s Corner, we head out with Wanderlust Tours for their Moonlight Snowshoe Tour.
As if trudging through a glittering snowfield under a blanket of stars wasn’t magical enough, we do it with a naturalist guide who dazzles our brains with info about local wildlife and the astral wonders above.
Our ultimate destination is a hand-carved amphitheater in the snow, complete with roaring bonfire and sweet treats served with mugs of cocoa and local spirits. Warmed from the inside, we trudge back to the van for a ride down the mountain, followed by sweet dreams all around.
It’s vacation after all, so today’s the day to be chill. We start in the Old Mill District for scrumptious brunch at Boxwood Kitchen, where we may or may not engage in a brutal thumb wrestling battle over who gets the biggest bites of tres leches French toast, polenta and eggs, and their to-die-for brussels sprouts with ponzu, sesame, and lime.
Next, it’s time for pampering. The newly-opened Radiant Day Spa is right there in the Old Mill and offers a scrumptious side of mountain views to go with that massage or facial.
If we’ve got time for one last hike, we’ll head for the Oregon Badlands Wilderness for epic desert landscapes dotted with craggy volcanic formations. There’s also the option to hoof it a couple miles to the trailhead at Tumalo Falls for a visit with the splashy, 97-foot marvel.
Congratulations, folks. We’ve done the ever lovin’ heck out of Bend, Oregon.