FEATURED WATERBURY EVENTS

 

Waterbury is home to a number of fun, festive, and quirky events and promotions! Here's a sampling of events to plan your visit around; check with event organizers or visit our Events Calendar for exact dates and details.

 

BROWSE MORE EVENTS ON THE FULL CALENDAR!

 

Waterbury, Vermont's 250th Anniversary logo

WATERBURY, VT 250 CELEBRATIONS

ONGOING, 2026 & 2027

The years 2026 and 2027 mark an extraordinary 250 years in the histories of the United States and Vermont. 2026 celebrates the formation of the United States of America with the anniversary of the signing of the Declaration of Independence, while 2027 marks the 250th anniversary of the founding of the Republic of Vermont. Events and activities throughout both years, both long-standing and new, will commemorate these milestones.

 

Spring

 

Bikers during the Gravel GrindGravel Grinder

may 3, 2026

Join mountain biking enthusiasts for this spring bike ride on Waterbury's dirt roads, which supports the work of the Waterbury Area Trail Alliance to build and maintain Waterbury's trails.

 

 

SUMMER

 

WATERBURY FLEA MARKET

SATURDAYS & SUNDAYS, MAY - OCTOBER, 2026

This is Vermont's largest and longest-running outdoor flea market, and each weekend packs Farr's Field with vendors selling antiques, sporting equipment, collectibles, arts & crafts, ephemera, oddities, and so much more!

 

 

Individuals walking through in Jack's Alley in downtown WaterburyPASSEGGIATA

WEDNESDAYS, MAY 27 - fall, 2026

Join in Waterbury's weekly passeggiata on Wednesday evenings from around 5:30-8:30 pm in the warm months! Stroll around town, chat with a neighbor, stop for a snack or drink, and just enjoy the community.

 

 

A band performing at a Concert in the ParkCONCERTS IN THE PARK

THURSDAYS, JUNE 11 - AUGUST 13, 2026

Put on by the Waterbury Rotary Club, this free annual concert series coincides with the time and location of the Waterbury Farmers Market, making it the place to be on Thursday nights in the summer!

 

 

People and a dog are dressed up and marching in the Not Quite Independence Day paradeNOT QUITE INDEPENDENCE DAY PARADE

JUNE 27, 2026

Waterbury typically kicks off the Independence Day celebrations a little early on the Saturday before the Fourth of July. The streets of Waterbury are shut down for the lively NQID parade and then spill over to a concert, fun family activities, and fireworks! This event is organized by the Waterbury Rotary Club.

 

 

Individuals waving to a train from the Waterbury Station platformTRAIN DAY

JUNE 27, 2026

All aboard for Train Day, Waterbury’s celebration of all things rail! A family-friendly event, the 1875 train station will host working model train displays, presentations and storytelling highlighting Waterbury’s train heritage, hands-on kid’s activities, and an all-ages trackless train ride around town.

 

 

Enjoying music on the lawn at the Waterbury Arts Fest Friday Night Block PartyWATERBURY ARTS FEST

JULY 10 - 11, 2026

This arts festival delivers fun for everyone and is a showcase for local art, food, and entertainment, making it a signature summer event in Waterbury. The festivities include the Friday Night Block Party, with great food, a beer garden, and music for dancing under the stars and Saturday's Arts Fest, an open-air arts and crafts market with over 100 vendors selling their locally crafted wares.

 

 

A line of antique cars at the Antique and Classic Car ShowVERMONT ANTIQUE AND CLASSIC CAR SHOW

AUGUST 7 - 9, 2026

The Car Show is one of the largest and oldest in New England and is a cherished summer tradition in Vermont. Some of the events that take place include automobile judging, a flea market & car corral, and Cruisin' Route 100 event.

 

Fall

 

Runners at the Leaf Peepers raceLEAF PEEPERS HALF MARATHON & 5K

October 4, 2026

For over 30 years, the Leaf Peepers Half Marathon and 5k races have taken place in Waterbury. This autumn event highlights the athletic and outdoorsy nature of our town!

 

 

Winter

 

A shopping promotion card for Wrap It Up and WinVery Merry Waterbury

MId-November - Mid-December, 2026

We roll out the red carpet every holiday season, with a variety of events and promotions under the Very Merry Waterbury umbrella, including the Wrap It Up & Win shopping and dining promotion, Holiday Stroll, River of Light Lantern Parade, and Artisans Boutique.

 

 

Lanterns at the River of Light paradeRiver of Light Lantern Parade

december 5, 2026

Since 2010, a group of local artists, students, and community members have made beautiful and elaborate lanterns, which are then paraded through downtown.

 

 

 

Human bowling during Waterbury WinterfestWaterbury Winterfest

Late January - Early February, 2027

This ten-day festival in the heart of winter includes great activities for all ages, such as broomball, human bowling, moonlight snowshoeing and skiing, ice sculpting, Wassailing, and much more!