Best events in
Pittsfield

When the day on the slopes or trails winds down, there are many events and things to do in Pittsfield, VT and the surrounding Green Mountains. The local scene ranges from intimate community gatherings in Pittsfield village to major concerts and festivals in nearby Killington. Rutland's historic downtown also provides a walkable center for arts, markets, and seasonal street fairs.

The energy in Killington shifts from daytime mountain sports to a lively après-ski scene, with live music at base lodges and late-night shows at venues like the Pickle Barrel and Wobbly Barn.
Downtown Rutland hosts recurring community celebrations, including the seasonal Art in the Park festival and the year-round Rutland County Farmers' Market.
Pittsfield fosters a close-knit feel with gatherings at the Roger Clark Memorial Library and annual traditions like Green Up Day and the Memorial Day Parade.

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Check ticket price on event

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Tuesday • 2:00 PM EDT

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Saturday • 12:00 AM CDT

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Sat, Oct 3 • 10:00 AM PDT

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Wed, Oct 7 • 7:30 PM GMT+1

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Events near Pittsfield

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Wilson Castle: A Paranormal Documentary Experience in Proctor, VT

Sat, Oct 3 • 2:00 PM

Wilson Castle

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Dine With the Dead: Wilson Castle Sleep Over Edition

Sat, Oct 10 • 6:00 PM

Wilson Castle

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The Fur Ball 2026: Rescue Never Sounded so Good

Sat, Oct 10 • 7:00 PM

Woodstock Town Hall Theatre

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Wed, Oct 21 • 8:00 AM

Rutland Regional Medical Center

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2026 Wobbly Barn Halloween Party

Sat, Oct 31 • 8:00 PM

Wobbly Barn

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NASW VT 2026 Conference

Thu, Nov 12 • 8:00 AM

Killington Grand Resort

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13th Annual Thanksgiving Killington $319 (2 Nights + Transport)

Fri, Nov 27 • 4:00 PM

Killington Resort

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Mihalidaze presented by Fiddlehead

Fri, Dec 4 • 8:00 PM

Pickle Barrel Nightclub

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Wilson Castle: A Paranormal Documentary Experience in Proctor, VT

Sat, Oct 3 • 2:00 PM

Wilson Castle

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Dine With the Dead: Wilson Castle Sleep Over Edition

Sat, Oct 10 • 6:00 PM

Wilson Castle

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The Fur Ball 2026: Rescue Never Sounded so Good

Sat, Oct 10 • 7:00 PM

Woodstock Town Hall Theatre

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Solheim CEN Review Course

Wed, Oct 21 • 8:00 AM

Rutland Regional Medical Center

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2026 Wobbly Barn Halloween Party

Sat, Oct 31 • 8:00 PM

Wobbly Barn

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NASW VT 2026 Conference

Thu, Nov 12 • 8:00 AM

Killington Grand Resort

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13th Annual Thanksgiving Killington $319 (2 Nights + Transport)

Fri, Nov 27 • 4:00 PM

Killington Resort

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Frequently asked questions about Pittsfield

Where can I find live music events near Pittsfield?

Killington is the main hub for live music events, especially during the ski season. Venues like the Pickle Barrel Nightclub and Wobbly Barn host regular performances, and Killington Resort presents the free Cooler in the Mountains concert series during summer afternoons.

What is the nightlife like in the Killington area?

Killington offers a lively nightlife scene centered around its resort culture. The après-ski atmosphere at the base lodges transitions into late-night entertainment with live music at clubs like the Pickle Barrel and Wobbly Barn, which are popular after dark.

Are there family-friendly events in the area?

Downtown Rutland offers many family-friendly events, particularly in the summer. The Rutland County Farmers' Market is a popular weekend activity, and the seasonal Friday Night Live series fills the streets with music and community-focused fun.

What are some notable food and drink events in the region?

The area hosts major annual food and drink events centered around Killington. The Killington Brewfest is a large craft beer festival each fall, while Killington Uncorked brings wine tastings to the resort in the summer.

What's the local art scene like?

Rutland is the center for the local arts scene, anchored by the historic Paramount Theatre. The city also hosts Art in the Park, a fine arts and crafts festival that takes place twice a year in Main Street Park.

How can I find free things to do near Pittsfield?

Free events are common, especially during summer months. Killington Resort's Cooler in the Mountains is a free outdoor concert series, and Rutland's Friday Night Live brings free entertainment and music to the downtown area.

What kind of outdoor events are typical for the area?

Outdoor events reflect the region's focus on the seasons and community. Examples include Rutland's farmers' markets and street parties, Killington's outdoor concert series, and Pittsfield's annual Green Up Day, a town-wide clean-up event.

How do community events differ between Pittsfield and Rutland?

Pittsfield's social life revolves around smaller community events at the Town Hall and library. In contrast, Rutland hosts larger public events and festivals in its downtown, such as Art in the Park and performances at the Paramount Theatre.

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Nearby cities

Springfield

Shelburne

Lebanon

Hanover

Montpelier

Rutland

Middlebury

Westport

Manchester

White River Junction

Claremont

Whitehall

Elizabethtown

Bellows Falls

Woodstock

Northfield

New London

Pottersville

Vergennes

South Burlington

Ludlow

Waterbury

Barre

Brandon

Manchester Center

Stowe

Williamstown

South Royalton

Chester

Charlestown

Springfield

Shelburne

Lebanon

Hanover

Montpelier

Rutland

Middlebury

Westport

Manchester

White River Junction

Claremont

Whitehall

Elizabethtown

Bellows Falls

Woodstock

Northfield

New London

Pottersville

Vergennes

South Burlington

Ludlow

Waterbury

Barre

Brandon

Manchester Center

Stowe

Williamstown

South Royalton

Chester

Charlestown

Online Events

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A Norman stitch-up? The story behind the Bayeux Tapestry

(ONLINE) Women on the Move with Ann Patchett

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Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Online Group Reading - September 27

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A Norman stitch-up? The story behind the Bayeux Tapestry

(ONLINE) Women on the Move with Ann Patchett

Washington Crossing the Delaware / The Crossing - Film History Livestream