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Best events in
Windham

From lively downtowns to quiet village greens, there's no shortage of events and things to do in Windham, VT. The region's cultural life pulses with a strong arts scene in Brattleboro and a community-centered rhythm in smaller towns like Putney and Newfane. Seasonal shifts bring different energy, from outdoor summer festivals and autumn heritage events to the bustling après-ski culture of the winter.

An evening in downtown Brattleboro often flows from dinner to a show at a venue like The Stone Church or the historic Latchis Theatre.
Find community-focused arts programming, including puppetry and theater, at intimate venues like Sandglass Theater and Next Stage Arts Project in Putney.
Experience the lively après-ski atmosphere near Mount Snow with live music at spots like The Last Chair Bar & Grill or Valley Craft Ales.

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Events near Windham

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Comedian Bob Marley BRATTLEBORO VERMONT Friday November 6! primary image

Comedian Bob Marley BRATTLEBORO VERMONT Friday November 6!

Fri, Nov 6 • 7:30 PM

Latchis Theatre

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Cooper Foundation Fundraiser and Awards Dinner primary image

Cooper Foundation Fundraiser and Awards Dinner

Sat, Nov 7 • 5:30 PM

70 Spyglass Ln

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Paint Night at the Hartness House primary image

Paint Night at the Hartness House

Sat, Nov 7 • 6:00 PM

The Hartness House

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8th Annual Vermont Outdoor Economy Summit primary image

8th Annual Vermont Outdoor Economy Summit

Thu, Nov 12 • 8:00 AM

The Barn At Fox Run

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Make an Evergreen Wreath with Joanna primary image

Make an Evergreen Wreath with Joanna

Sat, Nov 21 • 10:00 AM

Gallery at the VAULT

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Ski-In/Ski-Out & Hot Tub: Dec 18-20 Okemo $359 (2 Nights + Transport) primary image

Ski-In/Ski-Out & Hot Tub: Dec 18-20 Okemo $359 (2 Nights + Transport)

Fri, Dec 18 • 4:00 PM

Okemo Mountain Resort

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Culinary Retreat: Three-Day Introduction to Natural Cheesemaking primary image

Culinary Retreat: Three-Day Introduction to Natural Cheesemaking

Mon, Mar 1 • 9:00 AM

Parish Hill Creamery

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Ludlow Wedding Show primary image

Ludlow Wedding Show

Sun, May 16 • 12:00 PM

Fox Run Golf Club

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Comedian Bob Marley BRATTLEBORO VERMONT Friday November 6! primary image

Comedian Bob Marley BRATTLEBORO VERMONT Friday November 6!

Fri, Nov 6 • 7:30 PM

Latchis Theatre

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Cooper Foundation Fundraiser and Awards Dinner primary image

Cooper Foundation Fundraiser and Awards Dinner

Sat, Nov 7 • 5:30 PM

70 Spyglass Ln

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Paint Night at the Hartness House primary image

Paint Night at the Hartness House

Sat, Nov 7 • 6:00 PM

The Hartness House

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8th Annual Vermont Outdoor Economy Summit primary image

8th Annual Vermont Outdoor Economy Summit

Thu, Nov 12 • 8:00 AM

The Barn At Fox Run

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Make an Evergreen Wreath with Joanna primary image

Make an Evergreen Wreath with Joanna

Sat, Nov 21 • 10:00 AM

Gallery at the VAULT

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Ski-In/Ski-Out & Hot Tub: Dec 18-20 Okemo $359 (2 Nights + Transport) primary image

Ski-In/Ski-Out & Hot Tub: Dec 18-20 Okemo $359 (2 Nights + Transport)

Fri, Dec 18 • 4:00 PM

Okemo Mountain Resort

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Culinary Retreat: Three-Day Introduction to Natural Cheesemaking primary image

Culinary Retreat: Three-Day Introduction to Natural Cheesemaking

Mon, Mar 1 • 9:00 AM

Parish Hill Creamery

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Ludlow Wedding Show primary image

Ludlow Wedding Show

Sun, May 16 • 12:00 PM

Fox Run Golf Club

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Nearby cities

Keene

28 miles away

Lebanon

41 miles away

Springfield

15 miles away

West Swanzey

29 miles away

Glens Falls

47 miles away

Hinsdale

24 miles away

North Bennington

31 miles away

Hanover

42 miles away

Hudson Falls

44 miles away

North Adams

39 miles away

Greenfield Town

41 miles away

Bennington

32 miles away

South Deerfield

49 miles away

Hoosick Falls

37 miles away

Manchester

18 miles away

Shelburne Falls

40 miles away

Claremont

24 miles away

Peterborough

44 miles away

Woodstock

32 miles away

Manchester Center

16 miles away

Williamstown

40 miles away

Winchendon

48 miles away

Turners Falls

40 miles away

Jaffrey

43 miles away

Warner

46 miles away

South Glens Falls

47 miles away

Saratoga Springs

50 miles away

Rutland

32 miles away

Bellows Falls

15 miles away

Brattleboro

22 miles away

Keene

28 miles away

Lebanon

41 miles away

Springfield

15 miles away

West Swanzey

29 miles away

Glens Falls

47 miles away

Hinsdale

24 miles away

North Bennington

31 miles away

Hanover

42 miles away

Hudson Falls

44 miles away

North Adams

39 miles away

Greenfield Town

41 miles away

Bennington

32 miles away

South Deerfield

49 miles away

Hoosick Falls

37 miles away

Manchester

18 miles away

Shelburne Falls

40 miles away

Claremont

24 miles away

Peterborough

44 miles away

Woodstock

32 miles away

Manchester Center

16 miles away

Williamstown

40 miles away

Winchendon

48 miles away

Turners Falls

40 miles away

Jaffrey

43 miles away

Warner

46 miles away

South Glens Falls

47 miles away

Saratoga Springs

50 miles away

Rutland

32 miles away

Bellows Falls

15 miles away

Brattleboro

22 miles away

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Humanitarian Water Engineering Fall 2026 primary image

Humanitarian Water Engineering Fall 2026

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thursday • 1:00 PM GMT

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Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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Gestion des données de recherche [en ligne, GDR101]

Wed, Nov 25 • 9:30 AM EST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Animation du débreffage - 17 décembre 2026 - En ligne

Thu, Dec 17 • 12:30 PM EST

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Humanitarian Water Engineering Fall 2026 primary image

Humanitarian Water Engineering Fall 2026

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No Title, No Permission, No Problem: Harnessing the Power of Influence primary image

No Title, No Permission, No Problem: Harnessing the Power of Influence

Thursday • 1:00 PM GMT

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Gestion de l’anxiété dans le traitement des troubles alimentaires primary image

Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training primary image

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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Gestion des données de recherche [en ligne, GDR101] primary image

Gestion des données de recherche [en ligne, GDR101]

Wed, Nov 25 • 9:30 AM EST

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The MI5 Archive: Official Secrets primary image

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Animation du débreffage - 17 décembre 2026 - En ligne primary image

Animation du débreffage - 17 décembre 2026 - En ligne

Thu, Dec 17 • 12:30 PM EST

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Windham

Where can I find live music events in Windham County?

The Stone Church in Brattleboro is a key venue for diverse live music. For a more intimate listening room experience, Stage 33 Live in Bellows Falls hosts various performances, while après-ski spots near Mount Snow like The Last Chair often feature bands.

What are some popular food and drink events in the Brattleboro area?

Retreat Farm hosts a popular weekly Food Truck Roundup during the summer. Beyond specific events, the Brattleboro Area Farmers' Market is a major weekly gathering with local produce and prepared foods, while breweries like Valley Craft Ales feature their own food pairings.

Are there any family-friendly events in the region?

Many community events are welcoming to all ages, like the annual Newfane Heritage Festival. Sandglass Theater in Putney offers engaging puppetry performances, and the seasonal farmers' markets in Brattleboro and Putney are also great outings for families.

How can I experience the local art scene in Windham, VT?

Brattleboro's Monthly Gallery Walk is a monthly event from May through December. The Brattleboro Museum & Art Center features rotating contemporary art exhibits, and smaller galleries can be found throughout downtowns like Wilmington and Bellows Falls.

What makes for a good date night in Windham, VT?

A classic date night could involve a film or performance at the Latchis Theatre in Brattleboro. Alternatively, catching a show at the Bellows Falls Opera House followed by a walk through the historic downtown offers a memorable evening out.

Can you suggest some free events in Windham, VT?

Many gallery walks, like Brattleboro's Monthly event, are free to attend. Exploring the various seasonal farmers' and flea markets, such as the Wilmington Antique and Flea Market, is another way to enjoy the local scene without an admission fee.

What is the nightlife like in the Windham region?

Nightlife often centers on live performances rather than dance clubs. Brattleboro has the most options, with venues like The Stone Church, while the Mount Snow area offers a lively après-ski scene with music at places like The Last Chair Bar & Grill.

Which outdoor events are popular in the area?

The region hosts numerous outdoor events, especially in warmer months. Retreat Farm offers outdoor concerts and food truck gatherings, and the Harris Hill Ski Jump is a major annual outdoor competition that draws large crowds each winter.