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 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.


February 17-18, 2018 – Harris Hill Ski Jump

Harris Hill Ski Jump

They don’t call this the Original Extreme Sport for nothing! This long-standing, two-day Brattleboro tradition is held on an Olympic-size, 90-meter hill. The Harris Hill Ski Jumping Competition offers spectators an opportunity to experience the Olympic sport of ski jumping up close in all its breathtaking, heart-stopping glory. A Brattleboro tradition since 1922.


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 Baconfest – Bacon, Blues + Brews
Check back for date!

Guilford Fairgrounds, Guilford, VT
Brattleboro Baconfest on Facebook

Bacon, blues and brews are featured at this annual family-friendly festival! Local vendors showcase their mouthwatering bacon recipes, Brattleboro’s own Whetstone Station pours their craft beer, and the Mark Manley band provides the Blues. The day begins with the Hog Jog, a 5K and 10K race. This event is sure to sizzle!

Brattleboro Baconfest Hog Jog – Check back for date!

Guilford Fairgrounds, Guilford, VT
Hog Jog at Baconfest

The race is held in conjunction with the Brattleboro Baconfest – Bacon, Blues + Brews. The 5K race kicks off at the Guilford Fairgrounds on Weatherhead Hollow Road in Guilford, VT and winds its way through the back roads of Guilford. 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!


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.


Jingle Bell Jog – Check back for date!

Downtown Brattleboro
Jingle Bell Jog

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!