• Sip & Shop @ Cask & Cork

    Cask & Cork 3 Elm Street, Waterbury, VT, United States

    Get a head start on your holiday shopping while supporting Waterbury Winterfest! Join us for a festive silent auction at Cask & Cork during their regular Friday wine tasting on December 12th from 4:00–6:30 p.m. Browse an exciting selection of prizes generously donated by local businesses, sip great wine, and enjoy a fun community evening. […]

  • Bluegrass Night

    Pro Pig Brewery 2 Elm Street, Waterbury, VT, United States

    Join us at the Pro Pig Brewery for an evening of foot-stomping fun! The music is indoors; however, there are outdoor fire pits to enjoy if you're bringing a pup! Donations to Winterfest and for the band are greatly appreciated. No registration required.

  • A History of the Mount Mansfield Ski Patrol – A Special Historical Society Presentation

    Waterbury Municipal Building Steele Community Room 28 N. Main Street, Waterbury, VT, United States

    Did you know that America’s oldest ski patrol started right here on Mt. Mansfield? This talk by local historian and researcher Brian Lindner tells the fascinating story of the Mt. Mansfield Ski Patrol—and how a local need for skier safety helped shape ski history nationwide. After the Civilian Conservation Corps cut Vermont’s first official ski […]

  • Wassailing

    Historic Downtown Waterbury Waterbury, VT

    Bored of the same old winter nights? Come join the ultimate downtown music crawl! Grab your friends, dress up, and bring your instruments (or just your singing voice) for a night full of music, laughs, and good vibes. This isn’t your average caroling—think funky beats, crazy costumes, and clever lyrics! From 6:00-8:00 PM, groups will […]

  • Winterfest Block Party

    Elm Street Elm Street, Waterbury, United States

    Winterfest Block Party event on Elm Street FEATURING: Beer and wine tasting and sales from Cask & Cork & The Tropic Brewing Live music at Pro Pig Chili and other snacks prepared by local chefs at Pro Pig Silent Auction for local merch and gift cards at Cask & Cork         If […]

  • Winterfest Block Party – Green Mountain Performing Arts Performance

    Elm Street Elm Street, Waterbury, United States

    Live Performance at the Block Party Join us on Friday, January 30 at 5:30 pm for a special outdoor performance by Green Mountain Performing Arts at the Winterfest Block Party. This lively, family-friendly performance will bring energy, creativity, and winter cheer to downtown as we celebrate together. Bundle up, grab a warm drink, and enjoy […]

  • Backcountry Film Night @ Grange Hall

    Grange Hall Cultural Center 317 Howard Ave, Waterbury Center, VT, United States

    The Winter Wildlands Alliance creates a Film series annually to promote Winter and getting outside. They focus on outdoor adventuring in Winter. There are 10 short films in the series that will be shown-the total length is 2 hours. There is a $10 entry fee per person  

    $10
  • Intro to TRX

    Concentric Fitness/Joey Clark 475 street Gallagher Acres, Waterbury, United States

    Unleash your strength with local fitness pro Joey Clark in this powerful intro TRX session! TRX—Total Body Resistance Exercise—isn’t just a workout… it’s a full-body training revolution. Using nothing but straps, gravity, and your own body, you’ll build strength, balance, mobility, core stability, and athletic coordination—all in one dynamic class. Small group — Big results. […]

  • Winter KidsFest

    Waterbury Public Library 28 N. Main Street, Waterbury, VT, United States

    Join the Waterbury Public Library and The Children's Room for a morning of indoor and outdoor fun planned just for the kids! Once again, we'll be hosting a sledding and snow play party behind the library, with fun crafts and games in the SAL Room of the Library. The event will be held between 10 […]

  • PARTY IN THE PARK – Fat Tire Demo Biking

    Rusty Parker Memorial Park Waterbury Village Historic District, Waterbury, VT, United States

    Party in the Park - Fat Tire Demo Biking Come learn the joy and excitement of biking in the snow with the stability and performance of a Fat Tire bike. Bring family and friends to try a free demo ride at the Waterbury Winterfest Party in the Park in Rusty Parker Memorial Park. Bicycle Express […]

  • PARTY IN THE PARK (Adjacent) – Winter Soccer

    State Complex Horseshoe 103 S. Main Street, Waterbury, VT, United States

    ***SNOW SOCCER HAS BEEN MOVED INDOORS AT BROOKSIDE PRIMARY SCHOOL*** Waterbury Winterfest, along with Waterbury Youth Soccer and Capital Soccer, present the return of Winter Soccer! This is a chance to get outside and beat the winter blues. There will be games and activities accommodating all age groups and competitive levels. Please join us Saturday […]

  • PARTY IN THE PARK – Winter Bocce Tournament

    Rusty Parker Memorial Park Waterbury Village Historic District, Waterbury, VT, United States

    Party in the Park - Winter Bocce Tournament Games begin at 2:00 p.m.   Teams of 4 compete for the top prize on the unpredictably tricky, slicky bocce courts in Rusty Parker Memorial Park! We'll have two courts going and the top teams from each court enter the championship bracket! Cost: $20/team The tournament is […]

    $20
  • PARTY IN THE PARK – Beer Tasting with The Tropic Brewing

    Rusty Parker Memorial Park Waterbury Village Historic District, Waterbury, VT, United States

    Beer tasting in the Gazebo at Rusty Parker Park! Join us during Party in the Park for beer tastings by The Tropic Brewing!Sip and savor a selection of craft beers from this local favorite while enjoying the festive atmosphere of Party in the Park. It’s the perfect chance to sample something new, chat with fellow […]

  • Game Show

    American Legion Post #59 16 Stowe Street, Waterbury, Vermont

    🎉 The Winterfest Game Show is Baaaack! 🎉 Get ready to compete, laugh, and amaze yourselves at a new Game Show event as part of Waterbury Winterfest 2026. Join us at American Legion Post #59 - Saturday, January 31st from 5:30-8:30pm for an exciting team-based trivia showdown. Prizes will be awarded to the top three teams—so […]

  • Ice Skating Disco

    The Ice Center 546 River Road, Waterbury, United States

    Looking for all the dancing royalty in Waterbury and beyond! Mark your calendars for Saturday, January 31 at the Ice Center. The event will benefit Waterbury Common Market with entry as a non-perishable food item, as well as Waterbury Winterfest with our 50/50 raffle! Prizes for best costume and for a karaoke contest. The event […]

  • Big Games

    Waterbury Municipal Building Steele Community Room 28 N. Main Street, Waterbury, VT, United States

    BIG GAMES ARE BACK! Come have some fun with MakerSphere in a family friendly event for all ages at the Steele Community Room in the Waterbury Municipal building! We're bringing back our life sized Candyland board game that is sweet as can be, as well as big Jenga and oversized playing cards for an easy […]

  • The Connector Trail Descent: Ski & Snowshoe Tour

    Blush Hill CC to Little River Park 141 Lonesome Trail, Waterbury, VT, United States

    Starting point: Blush Hill Country Club parking lot. Ski (XC & tele) and snowshoe participants are welcome to enjoy this delightful tour, which includes several sweet sidebar tree shots for backcountry telemarkers, picturesque giant rocks, and a steep twisting final descent that drops onto a lovely rolling finish with scenic views of multiple bends of […]

  • Ski-A-Thon

    Dascomb Rowe Field Pavilion 33 N. Main Street, Waterbury, VT, United States

    Join Brookside Primary School PTO and Waterbury Winterfest for a x-country Ski-A-Thon to be held at DASCOMB ROWE FIELD on Mainstreet in Waterbury on Sunday Feb. 1st, 1 pm – 3 pm.  There will be prizes and a groomed track to race around the field!  All ages are welcome!  Children must be accompanied by an […]