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Performance Events and Things to do in Pittsfield, MA

Democracy Rocks 2 with Natalie Merchant *OUTDOOR GARDEN SHOW*
Sun, Aug 16, 3:00 PM
Woodstock · Colony in The Garden
Democracy Rocks 2 with Natalie Merchant *OUTDOOR GARDEN SHOW*
Sun, Aug 16, 3:00 PM
Woodstock · Colony in The Garden
Jillith Fair - Loving Jill Sobule - A Pride Month Event
Fri, Jun 12, 7:00 PM
Woodstock · Colony
Jillith Fair - Loving Jill Sobule - A Pride Month Event
Fri, Jun 12, 7:00 PM
Woodstock · Colony
Jerry Garcia Birthday Bash w/ Gratefully Yours In The Garden!
Sat, Aug 1, 5:00 PM
Woodstock · Colony
Jerry Garcia Birthday Bash w/ Gratefully Yours In The Garden!
Sat, Aug 1, 5:00 PM
Woodstock · Colony
RAWdance presents the CONCEPT series: Hudson Valley Edition 2026
Fri, Jun 26, 7:30 PM + 2 more
Kingston · Senate Garage
RAWdance presents the CONCEPT series: Hudson Valley Edition 2026
Fri, Jun 26, 7:30 PM + 2 more
Kingston · Senate Garage
The Skatalites w/ Mona Freaka
Sat, Jun 27, 7:00 PM
Woodstock · Colony
The Skatalites w/ Mona Freaka
Sat, Jun 27, 7:00 PM
Woodstock · Colony
Sales end soon
Stay Proud and Drag On! Saratoga Winery's Third Annual Drag Brunch
Sunday at 10:00 AM + 2 more
Saratoga Springs · The Saratoga Winery
Sales end soon
Stay Proud and Drag On! Saratoga Winery's Third Annual Drag Brunch
Sunday at 10:00 AM + 2 more
Saratoga Springs · The Saratoga Winery
Doug Howard's "Summer of '72" w/ Special Guest MaryLou Arnold-Gress
Thu, Jun 11, 7:00 PM
Woodstock · Colony
Doug Howard's "Summer of '72" w/ Special Guest MaryLou Arnold-Gress
Thu, Jun 11, 7:00 PM
Woodstock · Colony
Tu-Ner ft. members of King Crimson
Wed, Jul 29, 7:00 PM
Woodstock · Colony
Tu-Ner ft. members of King Crimson
Wed, Jul 29, 7:00 PM
Woodstock · Colony
The Wildwoods
Sat, Jul 18, 4:00 PM
Saratoga Springs · Caffe Lena
The Wildwoods
Sat, Jul 18, 4:00 PM
Saratoga Springs · Caffe Lena
New York State Writers Institute Fiction and Poetry Reading
Thu, Jun 25, 8:00 PM
Saratoga Springs · Caffe Lena
New York State Writers Institute Fiction and Poetry Reading
Thu, Jun 25, 8:00 PM
Saratoga Springs · Caffe Lena
Punk Night featuring Mickey Leigh's Mutated Music and more!
Thu, Jun 18, 7:00 PM
Woodstock · Colony
Punk Night featuring Mickey Leigh's Mutated Music and more!
Thu, Jun 18, 7:00 PM
Woodstock · Colony
'The Niall Connolly Band' In The Garden
Saturday at 6:00 PM
Woodstock · Colony
'The Niall Connolly Band' In The Garden
Saturday at 6:00 PM
Woodstock · Colony
The 420 Funk Mob's Super Melt Down Trip Fest (ft. Clip Payne)
Fri, Jun 26, 7:00 PM
Woodstock · Colony
The 420 Funk Mob's Super Melt Down Trip Fest (ft. Clip Payne)
Fri, Jun 26, 7:00 PM
Woodstock · Colony
The Sweet Clementines
Today at 7:00 PM
Woodstock · Colony
The Sweet Clementines
Today at 7:00 PM
Woodstock · Colony
Crystal Ship - A Tribute To The Doors
Sat, Jul 25, 7:00 PM
Woodstock · Colony
Crystal Ship - A Tribute To The Doors
Sat, Jul 25, 7:00 PM
Woodstock · Colony
2026 Hudson Valley Wine & Food Festival
Sat, Sep 12, 11:00 AM
Rhinebeck · Dutchess County Fairgrounds, U.S. 9, Rhinebeck, NY, USA
2026 Hudson Valley Wine & Food Festival
Sat, Sep 12, 11:00 AM
Rhinebeck · Dutchess County Fairgrounds, U.S. 9, Rhinebeck, NY, USA
Glen David Andrews
Thu, Aug 27, 7:00 PM
Saratoga Springs · Caffe Lena
Glen David Andrews
Thu, Aug 27, 7:00 PM
Saratoga Springs · Caffe Lena
The Gothard Sisters
Sun, Sep 13, 7:00 PM
Saratoga Springs · Caffe Lena
The Gothard Sisters
Sun, Sep 13, 7:00 PM
Saratoga Springs · Caffe Lena
5th Annual Michael Simmons Music Festival
Sat, Sep 26, 2:00 PM
Weatogue · Talcott Mountain Collective
5th Annual Michael Simmons Music Festival
Sat, Sep 26, 2:00 PM
Weatogue · Talcott Mountain Collective
Dive Presents: Pearl And The Oysters, Abyssmals & Griff @ Saratoga Arts
Thu, Jul 23, 7:00 PM
Saratoga Springs · Saratoga Arts
Dive Presents: Pearl And The Oysters, Abyssmals & Griff @ Saratoga Arts
Thu, Jul 23, 7:00 PM
Saratoga Springs · Saratoga Arts

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