Bundle Up for Waterbury Winterfest 2026: A Celebration Like No Other
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January 28 – February 1, 2026
The magic of winter is calling, and Waterbury Winterfest 2026 has been working behind the scenes to deliver an unforgettable experience.
From January 28 to February 1, come out and celebrate 16 years of frosty fun, community spirit, and winter recreation in the heart of Vermont.
Waterbury Winterfest is a celebration of everything that makes winter in Vermont extraordinary.
With proceeds benefiting scholarships, grants, and recreational activities in our beloved community, every laugh, every bite, and every cheer supports a greater cause.
Winterfest isn’t about one marquee event. It’s about movement through town, shared experiences, and the way winter has a knack for bringing people together when you least expect it.
A midweek kickoff with music and stories
Winterfest opens on Wednesday night with Bluegrass Night at Pro Pig Brewery.
The music is indoors, the fire pits glow outside, and the vibe is equal parts foot-stomping and laid-back. You may show up “just for a song” and end up staying for the whole set.
On Thursday, come out for a fascinating presentation on the history of the Mount Mansfield Ski Patrol. Local historian Brian Lindner traces how a very real need for skier safety on Vermont’s highest peak helped shape ski culture across the country, eventually influencing the formation of the National Ski Patrol and even the legendary 10th Mountain Division.
Wassailing, Waterbury-style
By Thursday night, Winterfest spills into the streets with Wassailing, a downtown music crawl that’s more than traditional caroling.
Groups fan out across town, performing at spots like Blackback Pub, Prohibition Pig, The Reservoir Tap Room, The Tropic Brewing, and the Old Stagecoach Inn before everyone converges for a big, joyful finale at the American Legion.
You don’t need musical credentials. You just need enthusiasm, maybe a costume, and a willingness to sing a little louder than usual.
Elm Street comes alive
Friday evening brings the Winterfest Block Party to Elm Street, transforming downtown into a hub of food, music, games, and good cheer.
Local chefs serve up comfort food, breweries pour winter warmers, and a silent auction offers a chance to scoop up local goods while supporting the festival’s mission. There are warm-up stations, carnival games for kids and adults, and live performances that keep the energy rolling well into the evening.
If you’re looking for a reason to wander downtown with a cup in hand and nowhere in particular to be, this is it.
Later that night, the celebration heads indoors with Backcountry Film Night at Grange Hall. Ten short films from the Winter Wildlands Alliance highlight winter adventuring and the joy of getting outside when conditions are less than perfect.
Saturday: winter, turned up to full volume
The day starts strong with fitness and family-friendly events, from an Intro to TRX class with local trainer Joey Clark to Winter KidsFest at the Waterbury Public Library, where sledding, snow play, crafts, and games take over the morning.
By late morning, the action shifts to Rusty Parker Memorial Park for Party in the Park. Fat tire bikes roll out for free demo rides on groomed trails, winter bocce teams battle slippery courts, and a beer tasting in the gazebo caps off the afternoon.
As evening falls, the energy moves back inside for the wildly popular Winterfest Game Show at the American Legion, followed closely by one of the most joyful events on the schedule: the Ice Skating Disco at the Ice Center. Costumes, karaoke, free skates while they last, and a food-drive entry make it feel like a party with a purpose.
A Sunday sendoff on snow
Winterfest wraps up on Sunday with events that celebrate movement, play, and community support.
Big Games at the Steele Community Room bring oversized board games and family-friendly competition indoors, while outdoor enthusiasts head out for the Connector Trail Descent, a guided ski and snowshoe tour through wooded singletrack with scenic views and a shuttle-assisted return.
The weekend closes with a Ski-A-Thon at Dascamb Rowe Field, supporting local youth ski programs and reminding everyone that winter recreation in Waterbury is something to be shared, learned, and passed along.
Why Winterfest matters
Waterbury Winterfest is about more than entertainment. Proceeds from events and sponsorships go directly toward scholarships, grants, and year-round recreational opportunities that benefit the community.
It’s a festival built by neighbors, for neighbors, with plenty of room for visitors to feel like locals for a few days.
If you’ve ever wished winter felt more connected, more playful, or more human, this is your invitation. Bundle up, wander downtown, try something new, and let Waterbury show you how good winter can be when it’s shared.
From the slopes to the streets, Waterbury Winterfest brings people together. Whether you’re a local or a visitor, this is your chance to experience the best of winter in Vermont—all while supporting a vibrant and growing community.
Mark Your Calendar
January 28 to February 1, 2026. More events and surprises are on the way, so be sure to visit Waterbury Winterfest for updates.
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Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers, an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.
