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Vermont Day Trips: Things to Do in Brattleboro, Vermont

With awesome hiking, skiing, biking, and more right here around Wilmington, plenty of visitors to the Hill are content to stay put once they arrive, and we can't blame them. Still, there's even more to be discovered on a short adventure downhill on Rt. 9. Within about a half hour's drive, you'll find a classic Vermont town with microbreweries, a vintage movie theater, a bursting arts scene, and plenty of family activities. These are just a few of our favorite things to do in Brattleboro, Vermont.  

Brattleboro, Vermont


Robb Family Farm

Even if you don’t have kids to take with you, the Robb Family Farm is a great way to experience some of Vermont’s most iconic traditions. The Robb Family Farm is a great way to see the process of making maple syrup and maple candies, and they also sell a variety of grass-fed, hormone-free meats to take home and enjoy.

Brattleboro Farmer’s Market

Each Saturday from spring until fall, vendors and shoppers take to the streets of Brattleboro for the weekly Farmer’s Market. More than 50 vendors selling produce, crafts, and food come together along with musicians and other entertainers to make this weekly event more of a celebration than a shopping trip. Come alone or bring the entire family – either way you’re sure to have a good time.

Shopping on Main Street

Looking for something for that special someone? Want to experience some authentic Vermont funkiness firsthand? Brattleboro’s Main Street shopping district won’t disappoint. Check out Beadnik’s for a unique and sometimes odd selection of gifts and curiosities, or take the kids to the Crafty Cauldron to make something firsthand. On your way home, swing by Twice Upon a Time to check out their huge selection of antiques and rarities from across Vermont and around the world.

Brattleboro Museum and Art Center Brattleboro Museum & Art Center

If you want to experience the culture and history of Vermont for yourself, look no further than the Brattleboro Museum and Art Center.  This museum, built from the shell of a former train station, showcases contemporary art with exhibits in all media, indoors and out. The museum also hosts frequent artist talks, concerts, and other cultural experiences, with either free or very modest admission prices. 

Brattleboro Retreat Trails

Feeling a little claustrophobic? Get out in the open on the Brattleboro Retreat Trails, a nine-mile network of hiking and multi-use trails that run right through town. These beautiful trails are well-maintained and easy to access, and they provide plenty of chances to get out and experience Vermont’s natural beauty. One of our favorites, the Tower Road, offers an awesome view of Brattleboro and the Connecticut River after only 15-20 minutes of hiking. 

Restaurants and Dining

In addition to the multitude of shopping and entertainment options in Brattleboro, there are also plenty of places to eat that will leave you feeling full without leaving your wallet empty. For casual food, great river views, and legendary house-made beers, check out Whetstone Station. Turquoise Grill has a top-notch burger along with Mediterranean and Turkish specialties. For date night, the two highest-end restaurants are Peter Havens and T.J. Buckley's

Brattleboro makes an easy day or evening trip, and it's right on your way if you're traveling to Chimney Hill via I-91. We highly recommend stopping in for dinner and a drink and leaving some time to wander around downtown. At one of our rental homes in Wilmington, VT, you'll have access to the perfect mix of mountain adventure and Vermont arts culture. 

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  1. Tyan on

    Ha, I guess you've got a point, it's not zero impact like snow sheoing. But these trails are only for snowmobiles, in the off season they're closed. There's no destruction going on if you stay on the trail.
    • P.O. BOX 415, 9 Haystack Road, Wilmington VT 05363