Valentine Card-Making
2025-12-01 11:00 - 13:00 (America/New_York) | Seminary Arts Center, 201 Hollow Road, Waterbury Center, Vermont, 05677
Join MakerSphere at the Green Mountain Seminary Building in Waterbury Center for a fun Valentine card making event!
Surprise your special someone with a handmade Valentine card they will be sure to treasure. We’ll be cutting, pasting, stamping, coloring, and making Valentine cards that you can give to the people you love.
Free family event for all ages (children under 8 must be accompanied by a parent).
No registration required.

VT Beer Quiz
2025-12-01 19:30 - 21:30 | Blackback Pub, 1 Stowe Street, Waterbury, VT, 05676, United States
The VT Beer Quiz returns to Blackback Pub!
Bring your taste buds and hop downtown to Waterbury’s friendly beer pub to enjoy this exciting event. The evening promises a bevy of bountiful brews bound to create a lingering taste sensation to last throughout the Winterfest season. Blackback Pub will have six IPAs to blind taste.
The cost is $12 per flight. Participants write down the correct beer and the winner receives a $50 gift certificate to Blackback Pub and a sweatshirt. In the event of a tie you will be placed into a drawing to choose the winner. In this circumstance the runner up will receive a hat.
No registration required.

Sip & Shop @ Cask & Cork
2025-12-12 17:00 - 19:00 | Cask & Cork, 3 Elm Street, Waterbury, VT, 05676, 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. Every dollar raised helps bring Winterfest 2026 to life and supports our local grant program.
We can’t wait to see you there!

Bluegrass Night
2026-01-28 17:00 - 19:30 | Pro Pig Brewery, 2 Elm Street, Waterbury, VT, 05676, 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
2026-01-29 17:30 - 18:30 | Waterbury Municipal Building Steele Community Room, 28 N. Main Street, Waterbury, VT, 05676, 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 trail on Mt. Mansfield, it quickly became clear that injured skiers needed a way to be rescued. A serious accident in 1933 changed everything, leading to the creation of the Mt. Mansfield Ski Patrol. By 1938, it became the model for the National Ski Patrol—and its influence didn’t stop there. The training and experience developed on Mt. Mansfield helped inspire the formation of America’s only ski troops during World War II: the legendary 10th Mountain Division. Along the way, you’ll meet the Waterbury men and women whose dedication and ingenuity put this Vermont mountain at the center of a national story.

No registration required. All Waterbury Historical Society programs are family-friendly, free, and open to the public.

Waterbury Historical Society is proud to partner with Winterfest for the second year.

Wassailing
2026-01-29 18:00 - 21:00 | Historic Downtown Waterbury, Waterbury, VT, 05676
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 perform at some of the coolest spots in town:

Blackback Pub
Prohibition Pig Brewery
The Reservoir Tap Room
The Tropic Brewing
Old Stagecoach Inn
The American Legion Post #59

At 8:00 PM, everyone comes together for an epic finale at the American Legion Post #59. Think massive singalongs, feel-good vibes, and a celebration of pure creativity. Sponsored by Stones Throw.
No experience needed! Got a group of friends? Awesome. Flying solo? No problem. Pro or amateur, all levels are welcome (even if you sing off-key). But hurry—only 7 groups can sign up, and spots go FAST!
Warmup your midwinter night and come join your friends and neighbors in this downtown tradition!
Register Your Group Here:
Registration for this event has closed. We hope you will come out to cheer on the performers!

Winterfest Block Party
2026-01-30 17:00 - 19:00 | Elm Street, Elm Street, Waterbury, 05676, 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 you would like to donate to the silent auction, please CLICK HERE
Performance by Green Mountain Performing Arts around 5:30pm
Warm up station at Rise Up Refill
Winter carnival games for adults and children including snow mini golf, reindeer ring toss, snowball pitching and snow bowling

Participating establishments include:
Prohibition Pig – chili and cornbread, beer tasting and sales
The Tropic Brewery – beer tasting and sales
Cask & Cork – beer and wine tasting and sales, *Silent Auction host*
Rise Up Refill – warm up station with warm drinks
Embody Physical Therapy – Carnival games and prizes

Winterfest Block Party - Green Mountain Performing Arts Performance
2026-01-30 17:30 - 18:00 | Elm Street, Elm Street, Waterbury, 05676, 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 this festive highlight of the evening!
About Green Mountain Performing Arts
Green Mountain Performing Arts (GMPA) is a Vermont-based 501(c)(3) nonprofit located in Waterbury, VT, offering year-round dance and theatre education for ages 3 through adult. Programs include classes, performance groups, after-school care, and summer camps.
GMPA’s mission is to enhance community cultural vitality through exceptional arts education in a supportive and creative environment. The organization is committed to equal access for all students, welcoming individuals with special needs and providing tuition assistance to families in need. With highly qualified, caring instructors and a wide range of classes for all ages and abilities, GMPA emphasizes both enjoyment and education—believing that joyful experiences in the performing arts inspire a lifelong connection to creativity.

Backcountry Film Night @ Grange Hall
2026-01-30 19:00 - 21:00 | Grange Hall Cultural Center, 317 Howard Ave, Waterbury Center, VT, 05677, 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

Intro to TRX
2026-01-31 09:00 - 10:00 | Concentric Fitness/Joey Clark, 475 street Gallagher Acres, Waterbury, 05676, 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. Only 6 spots available. Lock yours in ASAP and experience what smart training feels like.
Concentric Fitness is located at 475 Gallagher Acres, Waterbury.
Registration is required ensure your spot. The class is limited to 6 students.
We are sorry but the TRX class is full. Please check back in case someone cancels!

Winter KidsFest
2026-01-31 10:00 - 12:00 | Waterbury Public Library, 28 N. Main Street, Waterbury, VT, 05676, 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 am and noon on Saturday January 31, 2026. Bring sleds 🛷, snow ❄️ pants, and 😊smiles! Enjoy a bagel kindly donated by KC Bagels!

Registration is not required for this event.

PARTY IN THE PARK - Fat Tire Demo Biking
2026-01-31 11:00 - 15:00 | Rusty Parker Memorial Park, Waterbury Village Historic District, Waterbury, VT, 05676, 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 will provide demo fat bikes and helpful hints from trained professionals for riding the groomed trails surrounding Waterbury Village and Perry Hill Trails. Find out why so many are flocking to this winter sport!
No registration required. Participants must sign a waiver. You can download the waiver here to print and bring with you on the day of the event. Waiver forms will also be available on site.

PARTY IN THE PARK (Adjacent) - Winter Soccer
2026-01-31 12:00 - 14:00 | State Complex Horseshoe, 103 S. Main Street, Waterbury, VT, 05676, 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 Jan 31, 12pm – 2pm at Brookside Primary School. Learn more about Winterfest and the supporting organizations at the links below!
https://waterburywinterfest.com/
https://capitalsoccer.net/
https://waterburysoccer.com/

PARTY IN THE PARK - Winter Bocce Tournament
2026-01-31 14:00 - 16:00 | Rusty Parker Memorial Park, Waterbury Village Historic District, Waterbury, VT, 05676, 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 limited to 8 teams.
Register Here:

Team Captain/Primary Contact*

First

Last

Email Address*

Team Name PlayersPlease list your team members [first, last]. Teams consist of 4 players, including the team captain, and all players must be 18+.

Registration Payment HERE

PARTY IN THE PARK - Beer Tasting with The Tropic Brewing
2026-01-31 14:00 - 16:00 | Rusty Parker Memorial Park, Waterbury Village Historic District, Waterbury, VT, 05676, 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 beer lovers, and toast to a great day in the park. Cheers to good brews and even better company! 🍻

Game Show
2026-01-31 17:30 - 20:30 | American Legion Post #59, 16 Stowe Street, Waterbury, Vermont, 05676
🎉 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 bring your A-game!

Winterfest Game Show 2026 is currently SOLD OUT to competitors! To try your hand at the waitlist, please submit a registration without payment. If a spot opens up, we’ll be in touch in waitlist order! Of course, spectators are always welcome!

Team registration fee: $120
REGISTRATION IS REQUIRED FOR THIS VERY POPULAR EVENT as space is limited and we only have room for 12 TEAMS.
Team submissions will be accepted between now and 11:59 p.m. on Sunday January 18. Teams MUST have a minimum of 4 and maximum of 6 players, including the team captain/primary contact. Players may NOT be listed on more than one team roster. Teams with duplicate players or too few/too many players will be disqualified from the lottery. All players must be 18+.
Register HERE
Registration Fee Payment HERE

Ice Skating Disco
2026-01-31 18:00 - 20:00 | The Ice Center, 546 River Road, Waterbury, 05676, 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 is possible because of a great partnership with the Ice Center – with free skates available first come, first served!
Be there and be ready to groove in your skates!
Registration is not required for this event

Big Games
2026-02-01 11:00 - 13:00 | Waterbury Municipal Building Steele Community Room, 28 N. Main Street, Waterbury, VT, 05676, 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 elimination card game! We might even have something new in store!

Free family event for all ages (children under 8 must be accompanied by a parent).
No registration required.

The Connector Trail Descent: Ski & Snowshoe Tour
2026-02-01 11:00 - 14:00 | Blush Hill CC to Little River Park, 141 Lonesome Trail, Waterbury, VT, 05676, 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 the Little River. Cross the snow-machine bridge to a warm shuttle bus waiting to bring you back to the start.
The trek is between 3.0 and 3.5 miles. It is mostly single track trails and an old VAST route in the woods with a couple of short uphill climbs and quite a bit of downhill, including some steeper sections. Overall, we would rate the trail as moderate depending on snow conditions.
Carry a backpack with water, snacks, and extra layers.
This event aims to benefit Winterfest and the local VAST club, the Green Mountain Roamers, who can no longer afford to maintain the section of their trail that we will ski on this tour. Consider purchasing a membership to the Roamers or donating generously to Winterfest in support of their efforts.
No registration required. Participants must sign a waiver. You can download the waiver here to print and bring with you on the day of the event. Waiver forms will also be available on site.

Ski-A-Thon
2026-02-01 13:00 - 15:00 | Dascomb Rowe Field Pavilion, 33 N. Main Street, Waterbury, VT, 05676, 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 adult. Kids can use the BPS-provided skis and boots, and can pick them up during registration at the event. Waterbury Sports is offering 1/2 off rentals for adults, picked up on Saturdays at the store. While there is no fee to participate, a suggested $20 donation for families and $5 donation for individuals would be appreciated to support the PTO ski program. Let’s get out and ski together!
