Best events in
West Windsor

While the Upper Valley's rhythm is relaxed, there are many community-focused events and things to do in West Windsor, VT. The area's cultural life is centered in the historic village of Woodstock, with its classic town green and performing arts venues. Smaller surrounding towns like Windsor add to the scene with craft breweries and deep local history.

The picturesque village of Woodstock serves as the area's cultural hub, where an evening might include a performance at Pentangle Arts followed by a walk to a nearby restaurant.
In Windsor, the Artisan Park provides a more casual atmosphere, with spots like Harpoon Brewery frequently hosting live music and social gatherings.
Many events are deeply connected to the outdoors, from the weekly summer Feast and Field music series at Fable Farm to community activities at Ascutney Outdoors.

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Events near West Windsor

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8th Annual Vermont Outdoor Economy Summit

Thu, Nov 12 • 8:00 AM

The Barn At Fox Run

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NASW VT 2026 Conference

Thu, Nov 12 • 8:00 AM

Killington Grand Resort

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TNCC - Trauma Nursing Core Courses

Thu, Nov 19 • 7:30 AM

Dartmouth Hitchcock Medical Center

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Make an Evergreen Wreath with Joanna

Sat, Nov 21 • 10:00 AM

Gallery at the VAULT

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Pumpkin Rolls

Sun, Nov 22 • 12:00 PM

Coop Food Store—Lebanon

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Twin State Seminar 2026

Fri, Dec 4 • 7:30 AM

Hilton Garden Inn Hanover Lebanon

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Decorative Swag Making at King Farm

Sun, Dec 13 • 1:00 PM

King Farm Road

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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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8th Annual Vermont Outdoor Economy Summit

Thu, Nov 12 • 8:00 AM

The Barn At Fox Run

Check ticket price on event

NASW VT 2026 Conference

Thu, Nov 12 • 8:00 AM

Killington Grand Resort

Check ticket price on event

TNCC - Trauma Nursing Core Courses

Thu, Nov 19 • 7:30 AM

Dartmouth Hitchcock Medical Center

Check ticket price on event

Make an Evergreen Wreath with Joanna

Sat, Nov 21 • 10:00 AM

Gallery at the VAULT

Check ticket price on event

Pumpkin Rolls

Sun, Nov 22 • 12:00 PM

Coop Food Store—Lebanon

Check ticket price on event

Twin State Seminar 2026

Fri, Dec 4 • 7:30 AM

Hilton Garden Inn Hanover Lebanon

Check ticket price on event

Decorative Swag Making at King Farm

Sun, Dec 13 • 1:00 PM

King Farm Road

Check ticket price on event

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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Nearby cities

Keene

40 miles away

Lebanon

17 miles away

West Swanzey

43 miles away

Springfield

13 miles away

Franklin

42 miles away

Hinsdale

44 miles away

Hanover

18 miles away

Claremont

11 miles away

Barre

49 miles away

Bristol

38 miles away

Randolph

31 miles away

Rutland

26 miles away

Manchester

37 miles away

Woodstock

10 miles away

Northfield

47 miles away

Manchester Center

35 miles away

Plymouth

44 miles away

Newport

18 miles away

Warner

37 miles away

Peterborough

49 miles away

Bellows Falls

24 miles away

Brattleboro

42 miles away

Williamstown

44 miles away

White River Junction

14 miles away

Concord

47 miles away

Walpole

28 miles away

New London

26 miles away

Contoocook

43 miles away

Granville

39 miles away

Keene

40 miles away

Lebanon

17 miles away

West Swanzey

43 miles away

Springfield

13 miles away

Franklin

42 miles away

Hinsdale

44 miles away

Hanover

18 miles away

Claremont

11 miles away

Barre

49 miles away

Bristol

38 miles away

Randolph

31 miles away

Rutland

26 miles away

Manchester

37 miles away

Woodstock

10 miles away

Northfield

47 miles away

Manchester Center

35 miles away

Plymouth

44 miles away

Newport

18 miles away

Warner

37 miles away

Peterborough

49 miles away

Bellows Falls

24 miles away

Brattleboro

42 miles away

Williamstown

44 miles away

White River Junction

14 miles away

Concord

47 miles away

Walpole

28 miles away

New London

26 miles away

Contoocook

43 miles away

Granville

39 miles away

Online Events

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

Tomorrow • 1:00 PM GMT

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The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

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This Little World: a New History of Tudor and Stuart England

Wed, Nov 11 • 7:30 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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Corn as a partner and gift giver: Voices of respect

Wed, Nov 18 • 10:00 AM CST

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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

Tomorrow • 1:00 PM GMT

Check ticket price on event

The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

Check ticket price on event

This Little World: a New History of Tudor and Stuart England

Wed, Nov 11 • 7:30 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

Check ticket price on event

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

Check ticket price on event

Corn as a partner and gift giver: Voices of respect

Wed, Nov 18 • 10:00 AM CST

Check ticket price on event

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about West Windsor

Where are the best places for live music events near West Windsor?

Pentangle Arts in Woodstock hosts a variety of concerts in its historic Town Hall Theatre. For a more relaxed setting, Harpoon Brewery in Windsor is a popular spot for live music, and the weekly Feast and Field series offers outdoor music all summer.

Are there free events in the West Windsor area?

Yes, the region hosts several free community events, especially during summer months. The Music by the River series in Woodstock offers free concerts, and the Market on the Green often features live music without an admission fee.

What are some family-friendly things to do in the area?

Many local gatherings are great for all ages. Ascutney Outdoors hosts community events year-round, and the weekly Market on the Green in Woodstock provides a relaxed atmosphere with food vendors and local artisans that families can enjoy together.

Any recommendations for a date night in the Woodstock area?

A classic date night involves seeing a show at Pentangle Arts at the Woodstock Town Hall Theatre. The walkable village offers many cozy restaurants for dinner before or after a performance, creating a perfect evening out.

What kind of food and drink events happen around West Windsor?

The local scene celebrates farm-to-table culture with unique food events. The weekly summer Feast and Field series combines music with local food vendors, while Brownsville Butcher & Pantry occasionally hosts community cookouts featuring local ingredients.

Where can I find art and culture events?

Artistree Community Arts Center in nearby Pomfret is a great resource for workshops and performances. In Woodstock, Pentangle Arts presents a diverse calendar of film, theater, and music events at its central Town Hall Theatre location.

What are some popular outdoor events?

The area's natural landscape is a perfect backdrop for outdoor events. Ascutney Outdoors organizes community activities throughout the year, while Pentangle Arts' Music by the River series provides free concerts in Woodstock's East End Park during the summer.

What is there to do in Windsor?

Windsor offers a blend of Vermont history and local craft culture. Its Artisan Park is a popular destination with places like Harpoon Brewery, and the historic Windsor Station Restaurant provides a unique dining experience in a restored train depot.