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Brattleboro's Best Festivals

The best festivals in Brattleboro, in my view, are the authentic ones. They are quirky, have substance, are tied to the community, and exist due to local passion for the event. They go beyond tourism and marketing gimmicks and tap into something genuine and local.

I think these are some of the best Brattleboro festivals, listed in no particular order. What others did I forget?


Ski Jump

Standing in a snowy cornfield watching people fly off the ski jump on Cedar Street is about as authentic as it gets. The Harris Hill Ski Jump is one of Brattleboro’s older traditions.

Gallery Walk

Gallery Walk began as a marketing effort to improve downtown and has evolved into a monthly reason to go downtown and enjoy seeing friends and neighbors, hear some music, eat some snacks, and maybe even see some art.

Women’s Film Fest

A well-curated schedule of films by and about women, selected by a local team of reviewers, shown in our local theaters.

Lit Fest

Another well-curated series of events with top-notch authors and poets. Brattleboro has been a book-loving community since it began, and this festival fits right in.

Brew Fest

This is a new one, and I debate putting it on this list. On one hand, Brattleboro is home to quite a few beermaking establishments, so a beer festival makes sense. On the other hand, it seems a bit commercial and isn’t downtown - is it really for locals?

BrattRock Youth Rock Fest

A local music festival with a purpose - to showcase and encourage young, local musicians. This festival gets bonus points for the workshops it provides in addition to the performances.

Brattleboro West Arts

They say Brattleboro is an arts town, but West Brattleboro has the art tour, showing off a range of artistic talents at the studios and homes of the artists.


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Next Best Fests

Future Fest

Southern Vermont Dance Fest

Sporadic Ukulele Fests

Brattleboro Film Fest

The Stroll

Slow Living Dunnit

Tiny House Fest

Guilford Fair

Morris Dancers' May Day

Go Kart Race


Best Festivals of Guilford

As much as I like it, I think the Guilford Fair would have to be disqualified from the Brattleboro list.

If we had a Brattleboro Fair.... : ) (I want rides in town!)


Reporting In from the Greater Guilford Area

First off, all nice events, but some aren't actually "festivals," though maybe we need a definition.

But if the Guilford Fair (which is not identified as a festival, tho it has festive components) is to be included, then I would argue for inclusion of the Friends of Music at Guilford Labor Day Weekend Festival, an event about to take place for the I think 52nd year (I'm retired from the organization, tho still a helper, so I maybe have lost track of the number.) On the other hand, you called for a list of festivals in Brattleboro, and both the Friends of Music event & the festive Guilford Fair are in Guilford.

Or you could include the Marlboro Music Festival, and admit to fuzzy boundaries.

Is Harris Hill actually a festival? I thought more a sporting competition.


Brew Fest

I've worked as a volunteer at the Brattleboro Brew Fest several times. it's a lot of fun, and you get to meet many interesting people and learn a lot about beers, ales, ciders. Big local participation, many familiar faces, plus from all over New England. Well controlled generally, too, I've only seen a few incidents of excessive intoxication and/or obnoxiousness.


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