2020 Festivals, Parades and Fun!

The Greater Brattleboro Area is host to annual events that celebrate the arts, agriculture, literature, music, and film!  See below for all of the great reasons to plan a trip to Brattleboro.  Make sure to visit each event’s website for dates and times – and check out our calendar of events – planagogo – for more activities for the entire family!

First Friday of Every Month

Gallery Walk

Downtown Brattleboro

This festival of the arts features exhibit openings at galleries, eateries, and other businesses, most within a few blocks of Main Street.  Activities, street performances, and more – a festive block party.


Brattleboro Brewers Festival

VABEC 40 University Way, Brattleboro VT

This one day beer tasting event features some of the best craft brewers in Vermont, Massachusetts, New Hampshire and New York.  Brewers are on hand to share samples and meet their fans.



July 4 – Brattleboro Goes Fourth Independence Day Parade

10:00 a.m. – Parade marches through downtown Brattleboro
9:30 p.m. – Fireworks light up the sky at Living Memorial Park

For more information on the day’s family-friendly activities visit:
Brattleboro Goes Fourth on Facebook


October – Brattleboro Literary Festival


The Festival is a four-day celebration of those who read books, those who write books, and of the books themselves. The Festival includes readings, panel discussions, and special events, featuring emerging and established authors.


December – Jingle Bell Jog

Downtown Brattleboro

This 5K race kicks off at the Brooks House on Main Street.  Prizes are awarded to the top three men and women finishers and for best costume.  Holiday-themed attire is encouraged!  Jingle bells will be provided, along with Santa hats!. This race is family-friendly and professionally timed, so whether you are a serious runner or just want to have fun this is the race for you!

Find more fun things to do!

For more fun things to do in the greater Brattleboro area check out planagogo – the Chamber’s comprehensive online events calendar.  You won’t miss a thing!