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Southern Vermont Day Trips: Things to Do in Bennington, VT

History and scenery combine to make Bennington a quintessential American town. It's a great lunch stop on the way to Wilmington from New York, and if you haven't ventured down into the valley for a longer day trip there, we highly recommend it. There are plenty of things to do in Bennington, with attractions ranging from arts and history to shopping and drinks. Explore some of the best this southern Vermont town has to offer below.
Bennington Monument Vermont

The Bennington Museum

This classic Bennington, VT, attraction is one of the best places to learn about the history and culture of southern Vermont. The Bennington Museum features regional artwork, historical artifacts, and diverse special exhibits which highlight the many facets of Vermont and New England. You'll experience the history and beauty of this region over time and from many viewpoints through the collections housed in this historic museum. 

The Bennington Battle Monument

Commemorating one of the pivotal battles of the Revolutionary War, the Bennington Battle Monument stands as Vermont's tallest mandmade structure. At 306 feet, it offers stunning views of historic Bennington and the surrounding countryside — on a clear day, you can see to both New Hampshire and New York with ease. You'll also find a number of statues and other historic monuments in the surrounding park, making this a prime educational and cultural opportunity.

The Oldcastle Theatre Company

Whether you want to experience a unique-to-Vermont performance or simply need a night out, the Oldcastle Theatre Company has what you're looking for. Featuring many special productions and premieres during its summer and winter seasons, the Oldcastle Theatre Company stands as one of Bennington's oldest and most popular playhouses, and also as one of the best places to see a play in southern Vermont.

Bennington VT welcome sign The Shops at Camelot Village

Shopping is an American pastime, and it's no different here in Bennington. You'll find some of the best shopping in southern Vermont at the Shops at Camelot Village, a diverse and exciting shopping area in the heart of Bennington. Of special note is the Artisan Gallery, which features artworks and artisanal products from Bennington's own; and the Antique Center, a sprawling 25,000-square-foot antique market hosting more than 200 dealers. The Shops at Camelot Village are a perfect place to find gifts, souvenirs, and furnishings for your own home. 

Madison Brewing Company

After a long day of touring the town, you might want nothing more than a cold beer and some good food. You can find both at the Madison Brewing Company, a microbrewery and pub-style restaurant featuring six unique and delicious brews. The Madison Brewing Company has been a local favorite for more than 20 years, and once you stop in you'll see why. 
Your day trip to Bennington doesn't have to last just one day. Come back again tomorrow after staying in your own Vermont rental home at Chimney Hill. With comfortable amenities and a convenient location, your day trip might end up lasting a week. 

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  1. Luning on

    Hi Amanda, It's all about your lens and watching how the light falls. Taking lots and lots of pics and priactcing as much as you can will definately help. Also investing in a good, sharp lens that stops down to 1.8 or 1.4.Happy snapping! x
    • P.O. BOX 415, 9 Haystack Road, Wilmington VT 05363