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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
PAINT & SIP
Thursday at 6:00 PM
Lakeview Terrace · The Venue At Skyline
PAINT & SIP
Thursday at 6:00 PM
Lakeview Terrace · The Venue At Skyline
Tech in the Paddock: Streamlining Your Grazing Operations
Monday at 9:30 AM
Lakewood · 1Berkshire
Tech in the Paddock: Streamlining Your Grazing Operations
Monday at 9:30 AM
Lakewood · 1Berkshire
Lenox, MA September 10th!
Thursday at 7:30 PM
New Lenox · Antimony Brewing - Craft Brewery & Kitchen
Lenox, MA September 10th!
Thursday at 7:30 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
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
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
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
Halloween With Skeeter Creek At The Proprietor’s Lodge
Sat, Oct 31, 8:00 PM
Camp Merrill · 22 Waubeek Rd
Halloween With Skeeter Creek At The Proprietor’s Lodge
Sat, Oct 31, 8:00 PM
Camp Merrill · 22 Waubeek Rd
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
R.O.P.E. "Sweet Sixteen" Fundraiser
Sat, Sep 26, 6:00 PM
Lakewood · 74 First St
R.O.P.E. "Sweet Sixteen" Fundraiser
Sat, Sep 26, 6:00 PM
Lakewood · 74 First St
Queen For A Day
Thursday at 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
Queen For A Day
Thursday at 7:30 PM
Crane Lake Camp · The Foundry West Stockbridge
Comedy is Back at M&M's Tap & Tavern
Sat, Sep 19, 8:00 PM
New York · M&M'S Tap and Tavern
Comedy is Back at M&M's Tap & Tavern
Sat, Sep 19, 8:00 PM
New York · M&M'S Tap and Tavern
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
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
Wisdom Lodge Harvest Night at Hill Top Orchards
Sat, Nov 21, 5:30 PM
Massachusetts · Hilltop Orchards Home of Furnace Brook Winery and Jmash Cidery and The Taproom at Hilltop Orchards
Wisdom Lodge Harvest Night at Hill Top Orchards
Sat, Nov 21, 5:30 PM
Massachusetts · Hilltop Orchards Home of Furnace Brook Winery and Jmash Cidery and The Taproom at Hilltop Orchards
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
Lenox Wine Festival
Sat, Sep 19, 1:00 PM
Lenox · Pizzeria Boema
Lenox Wine Festival
Sat, Sep 19, 1:00 PM
Lenox · Pizzeria Boema
Bindlestiff Family Cirkus: "Mr. Pennygaff's Cirkus Sideshow Spectacular"
Sunday at 3:00 PM
Crane Lake Camp · The Foundry West Stockbridge
Bindlestiff Family Cirkus: "Mr. Pennygaff's Cirkus Sideshow Spectacular"
Sunday at 3:00 PM
Crane Lake Camp · The Foundry West Stockbridge
A Walk For Every Season Fundraiser Screening
Fri, Sep 25, 6:00 PM
New York · Soul Fire Farm
A Walk For Every Season Fundraiser Screening
Fri, Sep 25, 6:00 PM
New York · Soul Fire Farm

1 of 265

Things to do around Cheshire

Things to do in Albany

Things to do in Troy

Things to do in Saratoga Springs

Things to do in Springfield

Things to do in Schenectady

Things to do in Westfield

Things to do in Holyoke

Things to do in Hudson

Things to do in Easthampton Town

Things to do in Northampton

Things to do in Winsted

Things to do in Agawam Town

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!)

Tech in the Paddock: Streamlining Your Grazing Operations

Medium Night at Hilltop Orchards

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:

Lenox, MA September 10th!

Queen For A Day

Bindlestiff Family Cirkus: "Mr. Pennygaff's Cirkus Sideshow Spectacular"

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