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Events and Things to do in Cheshire, MA

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FreshGrass Presents Porchside Jubilee (Donate what you can!)
Sat, Oct 3, 2:00 PM
Houghtonville · The Porches Inn
FreshGrass Presents Porchside Jubilee (Donate what you can!)
Sat, Oct 3, 2:00 PM
Houghtonville · The Porches Inn
Open Stage Drag Night at Door Prize
Friday at 8:00 PM
Houghtonville · Door Prize
Open Stage Drag Night at Door Prize
Friday at 8:00 PM
Houghtonville · Door Prize
PAINT & SIP
Thu, Sep 10, 6:00 PM
Lakeview Terrace · The Venue At Skyline
PAINT & SIP
Thu, Sep 10, 6:00 PM
Lakeview Terrace · The Venue At Skyline
Lenox, MA September 10th!
Thu, Sep 10, 7:30 PM
New Lenox · Antimony Brewing - Craft Brewery & Kitchen
Lenox, MA September 10th!
Thu, Sep 10, 7:30 PM
New Lenox · Antimony Brewing - Craft Brewery & Kitchen
CULTIVATING RESISTANCE
Friday at 3:00 PM
New York · Soul Fire Farm
CULTIVATING RESISTANCE
Friday at 3:00 PM
New York · Soul Fire Farm
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Oct 17, 7:30 PM
Houghtonville · Bright Ideas Brewing
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Oct 17, 7:30 PM
Houghtonville · Bright Ideas Brewing
Paint & Sip– Wooden Serving Tray Workshop
Friday at 6:00 PM
Victory Hill · Tavern At The A
Paint & Sip– Wooden Serving Tray Workshop
Friday at 6:00 PM
Victory Hill · Tavern At The A
Garlic Town, USA Festival 2026
Saturday at 10:00 AM
Bennington · 113 Depot St
Garlic Town, USA Festival 2026
Saturday at 10:00 AM
Bennington · 113 Depot St
LULU FEST Berkshires 2026
Sat, Sep 19, 5:00 PM
Massachusetts · Lenox Meeting House
LULU FEST Berkshires 2026
Sat, Sep 19, 5:00 PM
Massachusetts · Lenox Meeting House
Tech in the Paddock: Streamlining Your Grazing Operations
Mon, Sep 14, 9:30 AM
Lakewood · 1Berkshire
Tech in the Paddock: Streamlining Your Grazing Operations
Mon, Sep 14, 9:30 AM
Lakewood · 1Berkshire
Chantell: Healing in Music
Sat, Oct 10, 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
Chantell: Healing in Music
Sat, Oct 10, 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
É.T.É
Sat, Sep 5, 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
É.T.É
Sat, Sep 5, 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
The Berkshire Coven: A Sanderson Sisters Spectacle
Fri, Oct 16, 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
The Berkshire Coven: A Sanderson Sisters Spectacle
Fri, Oct 16, 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
Then Is Now: 70's
Sat, Sep 19, 7:00 PM
Lakeview Terrace · The Venue At Skyline
Then Is Now: 70's
Sat, Sep 19, 7:00 PM
Lakeview Terrace · The Venue At Skyline
Misty Blues Band
Fri, Oct 2, 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
Misty Blues Band
Fri, Oct 2, 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
Lean Six Sigma Green Belt (LSSGB) Certification Training in Pittsfield, MA
Tue, Sep 22, 9:00 AM
Lakewood · Pittsfield, MA
Lean Six Sigma Green Belt (LSSGB) Certification Training in Pittsfield, MA
Tue, Sep 22, 9:00 AM
Lakewood · Pittsfield, MA
PMP Certification 4 Days Classroom Training in Pittsfield, MA
Tue, Sep 22, 9:00 AM
Lakewood · Pittsfield, MA
PMP Certification 4 Days Classroom Training in Pittsfield, MA
Tue, Sep 22, 9:00 AM
Lakewood · Pittsfield, MA
Oktoberfest Paint & Sip at Antimony Brewing
Thu, Oct 1, 7:00 PM
New Lenox · Antimony Brewing - Craft Brewery & Kitchen
Oktoberfest Paint & Sip at Antimony Brewing
Thu, Oct 1, 7:00 PM
New Lenox · Antimony Brewing - Craft Brewery & Kitchen
Medium Night at Hilltop Orchards
Sat, Oct 17, 7:00 PM
Massachusetts · Hilltop Orchards Home of Furnace Brook Winery and Jmash Cidery and The Taproom at Hilltop Orchards
Medium Night at Hilltop Orchards
Sat, Oct 17, 7:00 PM
Massachusetts · Hilltop Orchards Home of Furnace Brook Winery and Jmash Cidery and The Taproom at Hilltop Orchards
PMP (Project Management) Certification Training in Pittsfield, MA
Tue, Sep 22, 9:00 AM + 3 more
Lakewood · Regus Business Center
PMP (Project Management) Certification Training in Pittsfield, MA
Tue, Sep 22, 9:00 AM + 3 more
Lakewood · Regus Business Center

1 of 324

Things to do around Cheshire

Things to do in Albany

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Things to do in Saratoga Springs

Things to do in Pittsfield

Things to do in Northampton

Things to do in Schenectady

Things to do in Westfield

Things to do in Hudson

Things to do in Easthampton Town

Things to do in Holyoke

Things to do in North Amherst

Trends in Cheshire

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1. Winter holiday

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Frequently asked questions about Cheshire

What are the best events to attend?

According to Eventbrite, the best events are:

FreshGrass Presents Porchside Jubilee (Donate what you can!)

Lenox, MA September 10th!

Comedy On Tap at Bright Ideas Brewing in North Adams, MA!

Which events are currently trending in Cheshire?

The trending searches this month in Cheshire are:

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

CULTIVATING RESISTANCE

Paint & Sip– Wooden Serving Tray Workshop

Open Stage Drag Night at Door Prize

Garlic Town, USA Festival 2026

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