2018 Festivals, Parades and Fun!

The Greater Brattleboro Area is host to annual events that celebrate the arts, agriculture, literature, music, film and bacon – yes, bacon!  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.


May 26, 2018 – 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.


June 2-3, 2018 – Strolling of the Heifers

Brattleboro and surrounding venues
Strolling of the Heifers

Named one of the top 10 summers events in the country by Livability, this festival is built around a parade of heifer calves led by future farmers, followed by other animals, tractors, bands and floats.  The weekend includes a Friday evening street fair and a Sunday farm-to-farm “Tour de Heifer” cycling and farm tours.

June 23, 2018 – Tiny House Fest Vermont

Downtown Brattleboro, VT
Tiny House Fest Vermont

This street fest features a Pop-up Tiny House Village, Housing + Placemaking Academy, Building Arts Marketplace, Building Demos, Speed Design Reviews, Parklets, Performances, MakerSpace for kids & adults, and more!


July 4, 2018 – 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


Brattleboro Literary Festival – Check back for date!


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 8, 2018 – Jingle Bell Jog

Downtown Brattleboro

The 5K run and walk road race kicks off the Brooks House on Main Street and runs along the Whetstone Brook. Prizes are awarded to the first three men and women finishers. Holiday-themed attire is encouraged, but not required! Jingle bells will be provided. This is a family-friendly event, so whether you are a serious runner or just want to have fun this is the race for you!  For more information or to register click here!

Find more fun things to do!

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