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August 2019

Hemmings Cruise Ins – Most Thursday Nights All Summer Long

August 22 @ 5:00 pm - 8:00 pm
Hemmings, 222 Main St
Bennington, VT 05201 United States
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Hemmings Motor News – the old car hobbyist's Bible – is published right here in Bennington Vermont. On most 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…

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October 2019


October 5
Colgate Park, 1357 West Road
Bennington, VT 05201 United States
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octoberfest vermont event bennington pretzel stand

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. Photo Credit: Lorianna Weathers

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Fallapalooza – Fall Festival

October 26 @ 11:00 am - 3:00 pm
Downtown Bennington Bennington, VT 05201 United States + Google Map
pumpkins vermont fall festival fallapalooza

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

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November 2019

restaurant food, craft beer, burger, sandwich,

Shires of Vermont Restaurant Week – Annual Event

November 4 - November 8
Downtown Bennington, Bennington, VT 05201 United States + Google Map

Wonderful food and incredible deals for lunch or dinner at 17 restaurants throughout Bennington county. Reservations are highly recommended during The Shires of Vermont Restaurant Week. You might just need to stay the week to have time to try them all!

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