Things To Do Events


Hemmings Cruise-Ins – Thursday Nights all summer long

Hemmings Motor News – the old car hobbyist’s Bible – is published right here in Bennington Vermont. On Thursday evenings from May through September, you’ll see antique cars from Model-Ts to vintage Corvettes roll into the Hemmings headquarters and Old Car Museum. Enjoy popcorn, camaraderie and the coolest old cars you ever did see.

It’s just a day trip from Albany, New York, and less than one hour from the Berkshires. Come for the Cruise-in and stay through the weekend. The perfect Vermont Getaway.

Midnight Madness – Third Thursday in July

Come join the fun for Bennington’s annual Midnight Madness event — 56 years and running! Bennington’s entire downtown main street is all abuzz with live music, great food, and amazing deals while downtown stores open their doors until midnight.

And don’t forget to check out Four Corners North, where Hawkins House, Tap House at Catamount Glass and the world renowned Bennington Potters go all out with their Midnight Madness celebrations.

Garlic and Herb Festival – Annual Labor Day Weekend Event (Aug 31 – Sept 1, 2019)

Holy Garlic! Fifteen years and running and this Southern Vermont Festival keeps getting better and better. Garlic ice cream, garlic goodies, and other local delicacies  to eat on site and to take home. And, some of the best artisan vendors in the Northeast. This event is full to the brim with fun – Bounce houses, kiddy train, beer tents, live music and the Vermont Sun (?)

Bennington Arts Weekend – First weekend in August

It’s no wonder Bennington hosts the annual Arts and Craft show. After all Bennington was ranked in the top ten most vibrant arts communities by SMU’s National Center for Arts Research (NCAR) for the past two years running. This collection of the highest quality arts and crafts producers gather at Camelot Village every year for one of the Best Vermont Festivals around. Food, Family fun and amazing original arts and crafts.  Read more…

Quiltfest – Annual September Event

There’s a reason this show has been around for 26 years! Come for an action-packed weekend of education, challenge quilts, demonstrations and comradery in the beautiful green mountain state.

Food Truck Festival – Annual September Event

Just like it sounds! Head downtown where streets are blocked off for a food truck extravaganza. And a beer garden too.

Octoberfest – First Weekend in October (Oct. 6, 2019)

Colgate Park
1357 West Road
Bennington, VT 05201

A quintessential Octoberfest set against the backdrop of beautiful of Vermont mountains in their fall foliage glory. Ethnic Food. Beer Tent. Live Music. Artisan Vendors. German DJ. Children’s Activities. Wagon rides.

Fallapalooza – Last weekend in October

Live music and fun for the whole family as we waive goodbye to another beautiful Vermont foliage season. Join the celebration where main street is blocked off for the fun and festivities.

Winterfest – Annual January Event

The idyllic Vermont Village of North Bennington is the site of Winter fun for the annual Winter Festival. Come plunge in icy waters in the Penguin Plunge Event.

Winters Wings and Home Brew Festival – Annual March Event

Micro Brews, home brews are all the rage. And Bennington Vermont’s HomeBrew Festival gathers together a whole array of top notch home breweries and micro breweries for a party that will warm even the coldest winter day. And help decide who will be crowned the winner of the Best Wings in Bennington.

Bennington Battle Day Celebration and Parade

Monument Circle
Old Bennington, Vermont 05201


This is a weekend long celebration commemorating the Battle of Bennington which took place on August 16, 1777. It was a pivotal Revolutionary War battle which changed the course of history. Weekend events include a war re-enacter encampment at the Bennington Monument, a 5K race, a presentation by the Moodus Drum Fife & Drum Corps, a historic walk in Old Bennington, and a parade in downtown Bennington. Additional details on the Bennington Monument website.


Mayfest Arts and Craft Festival

Downtown Bennington

Mayfest is an annual street fair held in downtown Bennington featuring a wide variety of arts, crafts, activities, food, and entertainment. Families and people of all ages will find fun things to do and delicious food to eat.

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So much to do.