Waterbury embraces winter with Winterfest this week

January 24, 2026 | By Sarah Andrews | Correspondent

Lace up your boots and zip up your coats as Waterbury’s annual five-day Winterfest kicks off this Wednesday, Jan. 28, and runs through Sunday, Feb. 1, with a range of indoor and outdoor activities aimed to appeal to people of all ages and interests. 

After more than a decade, organizers work hard to make each year’s Winterfest even better than the last. 

Snow soccer is a unique Winterfest event for kids. Photo by Gordon Miller

This year’s schedule offers some of the always-popular events, like Bluegrass Night at Prohibition Pig on Wednesday, and the Winterfest Game Show returning to the American Legion on Saturday.

Organizing committee member Cheryl Casey says Wassailing is not to be missed. The time-honored Winterfest tradition invites rotating singing troupes to serenade diners at five downtown restaurants and pubs on Thursday evening, culminating in a friendly finale competition for the coveted Wassailing trophy at the American Legion. 

“There are certain events that couldn’t ever go,” Casey said. “Wassailing is one of those.”

Friday night brings the return of the Winterfest Block Party on Elm Street, with food, drink, and live music. Downtown businesses Prohibition Pig, Cask & Cork, Tropic Brewing, Paprika Empanada, and RiseUp refill are all participating in this year’s block party. There will be a silent auction at Cask & Cork, with gift cards and merchandise from local businesses. Youth dancers from Green Mountain Performing Arts are scheduled to perform at 5:30 p.m.

For those looking to get outside, Saturday’s schedule is packed, starting at 10 a.m. with Winter KidFest with sledding on the big hill behind the Waterbury Public Library at Dac Rowe Park. 

At 11 a.m., the Party in the Park gets underway with fat-tire bike demos and the popular Winter Bocce Tournament at Rusty Parker Memorial Park; Tropic Brewing will handle the beer tasting alongside these events. Over on the State Complex horseshoe lawn, kids can participate in Winter Soccer. 

Wassailing is one of Winterfest’s most popular indoor events. Photo by Gordon Miller

The party moves to the Waterbury Ice Center on Saturday night for the Ice Skating Disco that encourages costumes and includes a karaoke contest and a raffle (lots of prizes involved). Skate rentals are free, and there’s a collection for non-perishable food items for the Waterbury Common Market. 

This year, multiple Winterfest activities follow a backcountry theme. The Waterbury Historical Society plans a presentation on the History of the Mount Mansfield Ski Patrol on Thursday evening in the Steele Community Room at the municipal complex. 

On Saturday night, the Grange Hall Cultural Center in Waterbury Center hosts a Backcountry Film Night. The Winter Wildlands Alliance puts together an annual film series promoting outdoor winter adventures. This collection presents 10 short films over two hours. 

Two events will get people outside on Sunday. Cross-country skiers and snowshoers will trek the Connector Trail Descent three miles from the Blush Hill Country Club over the ridge and down to Little River. A shuttle bus brings participants back to Blush Hill. 

Downtown at Dac Rowe Park, the Brookside Primary School PTO hosts a x-c ski-a-thon fundraiser to support the school’s ski program. They will have skis for kids to borrow and adult rentals are available from Waterbury Sports.

MakerSphere has some indoor fun planned at the municipal complex, where all ages are invited to play giant versions of games including Vermont Candy Land and Big Jenga. 

Bocce at Rusty Parker Park is extra-challenging on snow. Photo by Gordon Miller

Winterfest is a non-profit event, organized by a small group of volunteers. The event is supported by the Waterbury Recreation Department. The event began as an opportunity for the community to connect during Vermont’s long, cold winters.

“It really brings people together, celebrating what there is to do as a community,” Casey said, “Even in the depths of winter.” 

Proceeds from the events and sponsorships fund grants awarded to community recreation organizations, helping to keep the cycle of Waterbury recreation thriving. 

Some events, including Wassailing, the Winter Bocce Tournament, and a Saturday morning TRX (Total Body Resistance) Exercise Class, require pre-registration due to capacity or planning purposes. The Winterfest Game Show is currently sold out to competitors, but there will be ample room for spectators to attend.

Most of the Winterfest activities are free of charge, with donations accepted. The Grange’s Backcountry Film Night is $10, and registration for the Winter Bocce Tournament is $20 per team. 

Find the full schedule of events on the Waterbury Winterfest website. Any last-minute updates due to weather or other changes will be noted there as well.