4 Seasons, 1 Town: Discover Brattleboro, Vermont

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Brittany Wilson
Curated By

Brittany Wilson

  • Vermont

  • Arts & Culture

  • Nature Escapes

  • Weekend Getaways

  • Off-the-Beaten-Path Travel

  • Small Towns

Advisor - 4 Seasons, 1 Town: Discover Brattleboro, Vermont
Curator’s statement

One of my favorite year-round city escapes, Brattleboro, Vermont, proves that New England is far more than just a fall foliage or winter ski destination. Immerse yourself in the local food scene at the Brattleboro Farmers’ Market or explore nearby farms to shop their farm stands or experience maple syrup production. Enjoy nature with hikes, swimming, or canoeing in the lakes. Wander through a lively downtown filled with unique shops, cozy cafés, museums, and colorful street art. Strike up a conversation with a local, or even stumble upon a peaceful protest, and you’ll quickly discover the thoughtful, fascinating spirit that makes this town so special.

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Where to stay in Brattleboro, Vermont

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Things to do in Brattleboro, Vermont

Robb Family Farm Sugarhouse

Lilac Ridge Farm

Visit the farm stand, and from May to August, get a Maple Creemee ice cream made from their very own cows' milk.

Robb Family Farm Sugar House

Take a tour of the sugar house and see how maple syrup is made.

Brattleboro Farmers' Market

A robust farmers' market. I'm not sure about the grocery shopping, but it's a great place to have breakfast or lunch and enjoy the fresh air.

Retreat Farm

Just outside of the main downtown strip, this farm is full of fun activities, hikes, and nature trails, including the start of the Retreat Tower Trailhead. It even has a bar with regional producers.

Vermont Canoe Touring Center

Rent gear to canoe, kayak, or paddleboard down the Connecticut River.

Brattleboro Museum + Art Center

Located in the center of town, on the river overlooking the iconic Gilbert Bridge. This museum curates local and international artists. Check out their events calendar for exciting events.

Vermont Center of Photography

Part of the thriving Brattleboro arts scene, this museum promotes photography through exhibits, education, and talks.

The Stone Church

Great music venue in a beautiful church with touring bands.

Vermont Insight Meditation Center

Riverfront meditation center with daily group meditation sessions. Check their website for special workshops and events.

Creamery Covered Bridge

Iconic red covered bridge. Bring a picnic of food from the farmers' market or Vermont Deli Store.

Places to eat & drink in Brattleboro, Vermont

Ube ice cream at Halo Hollow

T.J. Buckley’s

Fine dining featuring food from many local producers, an ever-changing menu, a carefully curated wine selection, and an open kitchen to watch the chef’s mastery in action.

Kipling’s Tavern

A cozy downtown tavern with delicious American-style food.

Halo Hollow

Downtown cafe featuring Filipino food, bubble tea, and incredible ube ice cream.

Mocha Joe’s

My personal favorite cafe in Brattleboro, Mocha Joe’s has the most unique and robust drink menu. They have their own organic farmer’s cooperative in West Africa to create fair-trade, organic, and sustainable fine coffee served in their shop.

Amy’s Bakery + Cafe

Great place to grab breakfast or lunch.

Brattleboro Food Co-Op

A community staple! Yes, this is a grocery store and no, you don’t have to be a member to shop. This is a great place to pick up some snacks, grab breakfast or lunch, and even find some special Vermont food you might want to bring home.

Vermont Country Deli

Stop here for incredible food, baked goods, and their country store. This place is popular so if you go on the weekend, be ready to stand in line and wait for parking. Is it worth it? I think so!

Vegan A.F.

A short walk up Canal Street from downtown, you’ll find Vegan A.F., a great place for delicious, vegan diner food. Be sure to try their award-winning chili!

Brittany Wilson

Travel Advisor

Brittany Wilson

Advisor - Brittany Wilson

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