The Ultimate Family Winter Weekend Itinerary in Bend, Oregon

A Family Winter Weekend Itinerary in Bend Built Around Adventure, Relaxation, and the Best of Bend in the Winter.

Winter in Bend is like something out of a fairy tale. Whether you're looking to explore the great outdoors or relax and unwind, Bend has everything you need for whatever type of winter stay you're looking for, from adrenaline-pumping outdoor adventures to cozy nights back at your Bend vacation rental. This family winter weekend itinerary in Bend is built around quality time enjoyed doing classic Bend winter activities.

Friday: Settle In & Ease Into the Weekend

3 pm | Arrive in Bend

Head Downtown and do a little walking around. Explore the shops, let the kids pick out a souvenir, and experience the beauty of Drake Park and Mirror Pond in the winter.

5 pm | Check In

Check in to your rental, unpack, freshen up, and head out for a laid-back family dinner, Bend style.

Bend has many incredible dining options. (See our dining guide.) Whether you want to grab-and-go or stay awhile, you can find what you're looking for without going far.

7 pm | Wind down

Back at the house, get into your cozies and kick off your weekend with hot cocoa and a movie.

Saturday: Snow Day ❄️

8 am | Pack up your snow gear and head out for breakfast and snacks

Fuel up for your adventure with a specialty coffee from Thump Coffee — then head to Sparrow Bakery for one of their famous Ocean Rolls. While you’re out, pick up a packable lunch for the day’s adventure. Sandwiches, pastries, and snacks travel well.

9 am | Head to Mount Bachelor ⛰️

From skiing and snowboarding to snowshoeing and dog sledding, Mount Bachelor has it all, including ski lessons for youngsters.

1 pm | Lunch and Hot Cocoa

Go somewhere warm, peel off wet layers, and recharge your batteries with hot cocoa and a yummy lunch.

2:30 pm | Mid-Day Reset

Head back to the rental to warm up and give everyone a chance to decompress. Nap, watch a movie, play games, whatever. The secret to a successful family weekend in Bend is scheduling time to rest between activities.

4:30 pm | Ice Skating

Head to The Pavilion for family ice skating. From October to April, you can enjoy recreational skating for all ages and abilities for $8 per person, including skate rental.

Saturday Evening | Cook In & Wind Down

Head back to the house and lean into a relaxed night at your Bend vacation rental. Cook something simple, or order in, and enjoy a cozy dinner at home.

Sunday: Brunch & High Desert Museum on the Way Out

10-11 am | Check out & head to brunch

On your way out of town, hit up one of our local family favorite brunch spots:

• McKay Cottage
• Victorian Cafe
• The Original Pancake House

12:00 pm | High Desert Museum

If you're looking to sneak in one last adventure before heading home, the High Desert Museum offers an exciting mix of indoor and outdoor activities for all ages. From cozy indoor exhibits showcasing native wildlife to winter-themed programs and hands-on history displays, there’s something for everyone. It's the perfect way to end your weekend in Central Oregon.

Where You Stay Matters

Staying somewhere like Juniper Getaway makes this kind of weekend effortless. A dog-friendly vacation home, outdoor space, and proximity to everything Central Oregon has to offer turn a great family winter weekend itinerary in Bend into a memorable one.

Winter weekends in Bend aren’t about cramming in activities — they’re about slowing down, eating well, and letting the season lead the way. Use this winter weekend itinerary in Bend to experience the ideal weekend getaway in Central Oregon.

View our Family-Friendly Winter Guide for more family friendly things to do in Bend and around Central Oregon in winter.