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Bennington Vermont Events and Festivals Abound | Summer and Fall 2019

Summer is right around the corner again which means it’s time to take a break and do a little planning for your Vermont getaways. From festivals to hiking, antiquing to museums; Bennington is chalked full of things to do this summer and fall. Below is a list of some of the most notable Bennington Vermont events and festivals. Dates to remember for sure, as you are planning your Southern Vermont Vacation!

hemmings motor news in Bennington, VT

Hemmings Motor News – producers of the “Bible of the Old Car Hobby”.

Thursdays, Summer 2019

Thursday Cruise-ins: Most every Thursday from May through August, Old Car lovers convene at Hemmings motor news —just down the street from our Vermont Bed and Breakfast. Each lively Cruise-in event is an open car show with awards, music and free popcorn. Plus, this is a perfect opportunity to visit the Hemmings museum display.

Thursday, July 18, 2019

56th annual Midnight Madness: We can’t begin to express how much fun this event is!  And it’s the perfect excuse for a girls getaway to Vermont. The world renowned Bennington Potters goes all out with their  Bennington Potters Midnight Madness celebration at Four Corners North. With pottery-filled tents, lively music, a bounce house  and fun for the whole family, the Potter’s Yard takes the Midnight-Madness-cake! You may have seen their world-class pottery in the likes of Ralph Lauren Home and Pottery Barn, but there is nothing like shopping straight-from-the-kiln with pottery hand-crafted right here in Bennington, Vermont.

And the fun doesn’t stop there! The entire of Bennington’s downtown main street is all a-flutter with great food, live music, and amazing deals as downtown stores open their doors until midnight.

bennington pottery midnight madness

Setting up for Bennington Pottery Midnight Madness. Photo from Bennington Potters.

Friday – Sunday, August 2 – 4, 2019:

Bennington Arts Weekend: featuring the Southern Vermont Art and Craft Festival: Come participate in a weekend full of cultural exchange. Bennington Arts Weekends offer activities and fun for all ages! There is a reason that Bennington was ranked as the 3rd most vibrant arts community in the U.S.  by SMU’s National Center for Arts Research (NCAR) in its annual Arts Vibrancy Index. The index ranks more than 900 communities across the country with populations from 10,000 – 50,000 . Our spot at number three, is a very prestigious designation that we in Bennington wear very proudly!

Saturday, August 3, 2019:   

Southern Vermont HomeBrew Festival: Featuring over fifty unique vendors, the Southern Vermont Summer HomeBrew Festival offers something for everyone: live music, delicious food, and a chance to sample the best micro-brew beer in the northeast!

Beer Trail in Bennington VT

Saturday and Sunday, August 16-18, 2019:


Bennington Battle Days: Come for the weekend of August 16-18, 2019 to celebrate this battle that was the turning point of the Revolutionary War. During the American Revolutionary War, Colonel Seth Warner and approximately 350 of his Green Mountain Boys, played a crucial role in defeating the British soldiers who came to capture the American supply depot in Bennington, Vermont. This battle which took place along the Walloomsac River on August 16, 1777, is considered by many to be the first win in the fight against the British and is a legal holiday in Vermont.

Walk from The Four Chimneys Inn to the Bennington Battle Monument — the most visited historic site in Vermont and the epicenter of all things Battle Days!

Saturday and Sunday, August 31 and September 1, 2019:

Garlic and Herb Festival: bowl of garlic cloves - Garlic Festival in VT

You’ll find garlic-everything at the Southern Vermont Garlic and Herb Festival. Mark your calendars for the 24th Annual Southern Vermont Garlic and Herb Festival happening in Bennington, Vermont August 31 and September 1, 2019. Enjoy a weekend full of everything garlic, plus a beer and wine garden, and fun family activities. Just kitty-corner from our historic Vermont inn, you can walk to the festivities. This is such a robust, fun-filled event that we wrote a whole blog post on it. Check out our blog post about the Southern Vermont Garlic and Herb Festival 

Saturday and Sunday, September 14 -15, 2019:

Bennington Quiltfest: Stop by Mount Anthony Union Middle School for the  26th Annual Bennington Quiltfest to check out an outstanding display of quilts created by quilters from all over the region.

Saturdays, May  – October, 2019    10 – 1pm 

fresh flowers in maple syrup bucket bennington vermont

Bennington Vermont Farmers Market You’ll find farm-fresh everything at the Bennington Farmers Market. There is nothing like fresh vegetables, lovely flowers and getting out to experience a bustling Farmers Market. Farming is at the heart and soul of Vermont Life. Your Vermont vacation is not complete without a trip to the farmers’ market! We love it so much, we even wrote a blog about the Bennington Farmers Market.  The Bennington Farmers Market, located at 150 Depot Street  is open from 10 pm to 1pm from May through October.

All Summer Long

Bennington, VT Bed and Breakfast - Woman Drinking Wine

Relax at The Four Chimneys Inn

Wrap your Vermont Summer Getaway plans around one of the many Bennington festivals and events scheduled for this summer. And don’t forget to save time to just relax at our historic Vermont inn. Book an incredible getaway at our top rated romantic Vermont inn and fall in love with Bennington!

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