Winter in Sisters, Oregon, isn't just a season; it's a magical wonderland of frosty fun! As fresh snowflakes blanket the town in a sparkling glow, there's an air of excitement that even the chill can't dampen. If you're dreaming of a winter that's more ‘thrill’ and less ‘chill’, then you're in luck! We're unwrapping the top 6 winter events of 2023-2024 that are so enthralling, they'll make a penguin jealous. So, grab your mittens and let's slide into a winter wonderland that promises more thrills than a sled ride down a snowy hill!
December 2 | 10am
Fir Street Park
Don your ugliest holiday sweater and bring the whole family to kick off the holiday season with a fun race through downtown Sisters. Now in its 3rd year, the annual Ugly Sweater event includes a friendly 5K race (or walk) with hot chocolate stations on-route, followed by a festive finisher party full of raffle prizes, complimentary beverages, an Ugly Sweater competition, and a visit from Santa! Online registration is required.
December 12 | 6pm to 8pm
Three Creeks Brewing Co.
Welcome the winter season with an avalanche of fun and prizes. Hosted by HooDoo Ski Area at our favorite local brewery, WinterVention is part of the Pacific Northwest’s biggest Snow Series Getaway. Play silly games, compete in SnOlympics, take a whack at Winter Trivia and throw down some Snowballers Bingo–all for the chance to win lift tickets, winter gear, skis, boards and more. Plus, sign up for your chance to win your very own pass to the Snowlab where you can design, build and shred your very own skis/board! This event is free to attend and fun for all ages.
Dirksen Derby 16 Snowboard Rally Race
December 15-17, 2023
Mt. Bachelor
This iconic event invites the international Snowboard and Sit-Ski communities together for an incredibly fun and memorable weekend full of strong friendships, intense competition, and fond memories. The goal of the Derby is to give everyone the chance to race down the same course — from the top pros to the youngest groms. Racers will take one timed run down either the Red or Green course on Saturday, then one timed run down the opposite course on Sunday for a final combined time. Fastest time wins!
Weekends | December 16, 2023 - March 31, 2024
Mt. Bachelor
Enjoy a FREE 90-minute interpretive tour to Learn about winter ecology at Mt. Bachelor and the geology of Central Oregon, the Deschutes National Forest watershed and the plants and animals found throughout this area. Led by an expert naturalist guide, these group snowshoe excursions are held at 10am and 1pm on Saturdays and Sundays throughout the winter season. Snowshoes are provided!
December 31 | 9am - midnight
HooDoo Ski Area
HooDoo’s annual NYE event is an all-day party on the mountain. Hosted by Bigfoot Beverages and Pepsi, the fun includes a full day of slope-shredding action, live music in the lodge, a special dinner menu, and an evening fireworks show to start the new year on a high note.
Fridays, January - March 2023 |4pm to 9pm
HooDoo Ski Area
Starting Friday, January 5, kick off your weekends at Central Oregon’s only night time ski destination. From 4pm to 9pm, shred the slopes under twinkling starlight that illuminates the powder with an ethereal glow. When you’re ski-ed out, enjoy hanging by the bonfire and listening to live music on the mountain.
February 16-18, 2024
The Old Mill, Bend, Oregon
Just a short 30-minute drive from Sisters in nearby Bend, experience the Northwest’s biggest winter festival with three full days of seasonal family fun. This gigantic winter event includes everything from ice carving competitions and unique fire sculptures to live music, family games and races, amusement rides, and a full array of arts and crafts vendors from all over the state. Tickets are good for all three days and can be purchased online at the event website.
Book your Winter Stay with Sisters Vacation Rentals
What better way to dive into these icy delights than by cozying up with Sisters Vacation Rentals? Nestled right in the heart of the festivities, our properties offer the perfect frost-covered doorstep to step out from and join the heartwarming action. How about a charming 2-bedroom condo with an indoor gas fireplace to chase away the winter chill? Or retreat to a rustic A-frame log cabin on the edge of a frost-tipped forest, where custom wood carvings and a warm pellet stove add warmth to those snowy winter evenings. Whatever suits your winter style, our team of local property experts is here to help you find the perfect homebase for these exciting winter events. Book your stay today!
