There are two kinds of Southern Vermont plans: the ones you make, and the ones you remember exist at the last possible second.

This list is for the second category.

Below are recurring markets, music nights, art walks, community events, and seasonal anchors around Brattleboro, Bennington, Manchester, Wilmington, Dover, Londonderry, Dorset, and the Deerfield Valley.

As always: check the event or venue link before you go. Weather, holidays, staffing, mud, and Vermont being Vermont can all change the plan.

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Weekly Markets

Brattleboro Area Farmers' Market

Saturdays, 9:00 AM-2:00 PM 

May-October 

570 Western Ave, Brattleboro

The big one. Local produce, prepared food, crafts, lunch, music, and the general feeling that you have made one good decision with your Saturday.

More info

Brattleboro Winter Farmers' Market

Saturdays, 10:00 AM-2:00 PM 

November-March 

Winston Prouty Campus, Brattleboro

When the outdoor market season ends, the winter market takes over: local food, baked goods, prepared foods, crafts, and a reason to leave the house when the sun has become a rumor.

More info

Bennington Community Farmers Market

Saturdays, 10:00 AM-2:00 PM 

Year-round 

239 Main Street, Bennington

Local vendors, live music, children’s programming, community events, and Bennington Community Market specials. Useful, central, and a good Saturday habit.

More info

Dorset Farmers Market

Sundays, 10:00 AM-2:00 PM 

Dorset

Producer-only market energy: produce, meats, cheeses, baked goods, flowers, prepared foods, crafts, and Vermont-made things from the people who actually made them.

More info

West River Farmers Market

Saturdays, 9:00 AM-1:00 PM 

May 23-October 10, 2026 

Intersection of Route 100 & Route 11, Londonderry

Farmers, food producers, artisans, prepared food, and a very good excuse to be in Londonderry on a Saturday morning.

More info

Art Walks, Music, and Going-Out Stuff

Brattleboro First Fridays & Gallery Walk

First Fridays, 5:00-9:00 PM 

May-December 

Downtown Brattleboro

Gallery Walk is back for the 2026 season with galleries, maker markets, food trucks, live music, public art, and the kind of downtown chaos Brattleboro does better than almost anywhere.

This year’s First Fridays include Elliot Street maker markets, live music in Harmony Lot, food trucks, a Lawson’s Finest beer garden, public art walks, and gallery openings throughout downtown.

More info

Local Music Showcase

Thursdays, 6:00 PM 

Bar 580, Brattleboro

A weekly no-cover showcase for local musicians at Bar 580 in the Vermont Marketplace. Good for people who want live music without needing to plan a whole dramatic night out.

More info

First Saturday Pub Sing at Marigold

First Saturday of the month, 3:00-6:00 PM 

Marigold, Brattleboro

A traditional pub sing hosted by Christine Kierstead. Low-pressure, communal, and very Brattleboro in the best way.

More info

Manchester Concerts on the Green

Free concerts, June-August 

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