You will find the true winter playground of Bend, Oregon tucked against the backdrop of the Cascade Mountains. The city combines its love for the outdoors with cozy small-town charm, creating a festive season filled with snow-dusted trails, warm fires, and community spirit when the holidays arrive. Whether you’re planning a holiday vacation or a month-long winter retreat, celebrating the holidays in Bend like a local means embracing both adventure and relaxation in perfect balance. Here are all of the wonderful ways to spend your Christmas in Bend getaway:
Enjoy the Snowy Outdoors
Locals in Bend know that winter is one of the best times to explore. Mount Bachelor is just a short drive away where skiing and snowboarding are part of daily life. The mountain offers everything from wide, groomed runs to terrain parks and scenic Nordic trails, providing something for everyone from seasoned skiers to first-timers.
Snowshoeing and cross-country skiing are perfect if you prefer something slower-paced and are great ways to experience the area’s peaceful beauty. Try the trails at Virginia Meissner Sno-Park or head to Wanoga Sno-Park for snowshoe loops that wind through towering pines. Families will enjoy a sledding hill and tubing area perfect for a day of fun in the snow.
Even downtown Bend gets a touch of winter magic. Take a walk along the Deschutes River Trail, where the snowy landscape sparkles in the sunlight, or go ice skating at The Pavilion that is a favorite local gathering spot during the holidays.
Celebrate with Local Festivities
Bend’s holiday season is full of community events that make the city feel warm and welcoming even in the cold. The annual Christmas Parade through downtown Bend brings colorful floats, marching bands, and plenty of holiday spirit to the streets. Just a few blocks away, the Old Mill District transforms into a winter wonderland with lights, live music, and festive shopping.
One of the most magical local traditions is the Holiday Lights Paddle Parade, where kayakers and paddle boarders deck out their gear with lights and float down the Deschutes River after dark. It’s a uniquely Bend experience that perfectly captures the town’s mix of adventure and creativity.
Visitors in December will not want to miss the Tree Lighting Ceremony in Drake Park or the Bend Winterfest in February that is a celebration that includes ice sculptures, live music, and local food vendors.
Savor Seasonal Flavors
Bend’s culinary scene thrives during the holidays offering everything from craft breweries to cozy restaurants serving hearty winter fare. Locals love places like Zydeco Kitchen for upscale comfort food or Jackson’s Corner for casual, locally sourced dishes.
For a festive night out, try one of Bend’s many breweries or cider houses, including Deschutes Brewery and Crux Fermentation Project that are local favorites. These often release special winter brews around the holidays just in time for the season.
Coffee lovers will also appreciate Bend’s thriving café culture; nothing beats warming up with a latte from a local roaster after a morning in the snow.
Local farmers markets and local specialty shops are perfect for picking up fresh produce, craft cheeses, and Oregon wines to use to create a stunning meal at your vacation rental. Preparing a holiday meal in your own kitchen, surrounded by friends and family, is a favorite local tradition.
Explore Downtown Bend
Downtown Bend takes on a special charm during the holidays. The streets are lined with twinkling lights, shop windows are decorated for the season, and local boutiques offer everything from handmade gifts to outdoor gear. It’s the perfect place to do your holiday shopping while supporting local artisans. Stop into one of Bend’s bakeries for a sweet treat or enjoy a leisurely lunch at a café with a view of the snowy Cascade peaks. Locals love the laid-back pace this time of year where it is all about slowing down and soaking in the magic of the season.
Relax and Recharge
There is nothing better after a day of exploring than returning to your vacation rental to warm up by the fire or soak in a private hot tub under the stars. Many of our rentals in Bend feature cozy mountain décor, large windows overlooking the pines, and easy access to the trails and slopes. Guests staying longer can consider adding a spa day to your itinerary. Bend is known for its wellness culture with several spas offering hot stone massages and steam rooms perfect for post-ski relaxation.
An Oregon Holiday to Remember
Celebrating the holidays in Bend like a local means embracing everything that makes this mountain town special. It is all about love for nature, creative spirit, and a sense of community. Come experience the cozy town charm during the holidays with one of our premier vacation rentals found here in the area. A new family tradition all starts with choosing Bend as your holiday destination this season.
