Top Things to Do in Brattleboro, Vermont

Chesterfield Inn, although located in New Hampshire, is a short 10-minute drive across the Connecticut River to the charming town of Brattleboro, Vermont. Spend time in town or on the river, the mountains, or the rambling trails in the woods. Brattleboro is a very vibrant place, with lots going on and many nooks and crannies to explore. It’s the perfect day trip during your next getaway! Here are our top recommendations for places to spend time while you’re in town.

two lattes on a table

Amy’s Bakery: A must-try place for a latte and an almond horn, or a baguette for lunch.

Vermont Artisan Designs: A magical place chock full of the finest art and objects crafted by Vermont artisans.

Latchis Theater: Featuring four screens in a an Art Deco building with movies and live shows, this is a must for any rainy day.

A book stack in the Brattleboro, VT bookstore

Everyone’s Books on Elliot Street: Nothing pairs with a vacation better than a book! Pick out a new story to get lost in while you’re relaxing at the Inn.

Grafton Cheese Company: A fabulous cheese factory and a shop full of edible delights. Indulge in the best!

Brattleboro Food Coop: The best place to meet the locals – much more than a grocery store!

Farmer's market in Brattleboro, Vermont

Farmer’s Market: Saturdays on Route 9 in West Brattleboro in the warm months. Farmers, food and fun!

Walker Farm: A heavenly oasis for flowers and plants as well as fresh, organic produce seasonally.

Twice Upon a Time: This authentic shop is the perfect place to search for unique antiques and collectibles you can’t find anywhere else

Couple walking in the woods in Brattleboro, Vermont

Brattleboro Retreat Trails to the Retreat Tower: This an idyllic place for a wonderful walk in the woods to the tower that overlooks Brattleboro. Take in the views!

Sam’s Outdoor Outfitters: The must-stop shop to pick up everything you need for your next New England outdoor adventure.

Guest Room at West Chester Inn

The Perfect Place to Stay & Dine

Make Chesterfield Inn your home away from home, and come back to our cozy and charming Inn after a full day of exploring Brattleboro. Relax in comfortable rooms, enjoy a hot meal at our on-site restaurant, and feel at peace. We are also happy to tailor an itinerary for you to use while you’re here! Just tell us about your interests at check-in and we’ll guide you to the best of the best.

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