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Events and Things to do in Cheshire, MA

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AQUANETT
Sat, Nov 21, 8:00 PM
Pittsfield · 22 Waubeek Rd
AQUANETT
Sat, Nov 21, 8:00 PM
Pittsfield · 22 Waubeek Rd
Wisdom Lodge Harvest Night at Hill Top Orchards
Sat, Nov 21, 5:30 PM
Richmond · 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
Richmond · Hilltop Orchards Home of Furnace Brook Winery and Jmash Cidery and The Taproom at Hilltop Orchards
NEW YEAR'S EVE
Thu, Dec 31, 6:00 PM
Pittsfield · Proprietor's Lodge
NEW YEAR'S EVE
Thu, Dec 31, 6:00 PM
Pittsfield · Proprietor's Lodge
BRING IN 2027 AT THE VENUE
Thu, Dec 31, 6:00 PM
Lanesborough · The Venue At Skyline
BRING IN 2027 AT THE VENUE
Thu, Dec 31, 6:00 PM
Lanesborough · The Venue At Skyline
Q-MoB Queer Men's Coffee Klatch @ Steeple City Social (North Adams, MA)
Sat, Nov 14, 10:00 AM + 6 more
North Adams · Steeple City Social
Q-MoB Queer Men's Coffee Klatch @ Steeple City Social (North Adams, MA)
Sat, Nov 14, 10:00 AM + 6 more
North Adams · Steeple City Social
Sales end soon
Pride Night w/ DJ PupDaddy @ Hot Plate Brewing (Pittsfield, MA)
Thursday at 7:00 PM + 6 more
Pittsfield · Hot Plate Brewing Co.
Sales end soon
Pride Night w/ DJ PupDaddy @ Hot Plate Brewing (Pittsfield, MA)
Thursday at 7:00 PM + 6 more
Pittsfield · Hot Plate Brewing Co.
Wacky Williamstown, MA Scavenger Hunt
Today at 11:00 AM + 779 more
Williamstown · Tunnel City Coffee
Wacky Williamstown, MA Scavenger Hunt
Today at 11:00 AM + 779 more
Williamstown · Tunnel City Coffee
New Lebanon Pie-Off
Sun, Nov 15, 4:00 PM
New Lebanon · Roaring 20s Brewery & Taphouse
New Lebanon Pie-Off
Sun, Nov 15, 4:00 PM
New Lebanon · Roaring 20s Brewery & Taphouse
Antimony Brewing Comedy Series w/ Nick Griffin
Thu, Nov 12, 7:30 PM
Lenox · Antimony Brewing
Antimony Brewing Comedy Series w/ Nick Griffin
Thu, Nov 12, 7:30 PM
Lenox · Antimony Brewing
Almost full
Out of the Darkest Forest
Thu, Nov 19, 7:00 PM + 2 more
Ashfield · Double Edge Theatre
Almost full
Out of the Darkest Forest
Thu, Nov 19, 7:00 PM + 2 more
Ashfield · Double Edge Theatre
Sales end soon
Q-MoB Queer Men's Coffee Klatch @ Wander (Pittsfield, MA)
Saturday at 10:00 AM + 13 more
Pittsfield · WANDER Berkshires
Sales end soon
Q-MoB Queer Men's Coffee Klatch @ Wander (Pittsfield, MA)
Saturday at 10:00 AM + 13 more
Pittsfield · WANDER Berkshires
Round the Regions Western Mass
Tue, Nov 10, 5:00 PM
North Adams · Casita
Round the Regions Western Mass
Tue, Nov 10, 5:00 PM
North Adams · Casita
Sales end soon
Penny Arcade: Longing Lasts Longer
Friday at 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Sales end soon
Penny Arcade: Longing Lasts Longer
Friday at 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Dec 19, 7:30 PM
North Adams · Bright Ideas Brewing
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Dec 19, 7:30 PM
North Adams · Bright Ideas Brewing
Sales end soon
Berkshire Inclusive Crafting Group @ Funky Phoenix (Pittsfield, MA)
Tomorrow at 5:30 PM + 6 more
Pittsfield · Affordable Bike Repair at The Funky Phoenix
Sales end soon
Berkshire Inclusive Crafting Group @ Funky Phoenix (Pittsfield, MA)
Tomorrow at 5:30 PM + 6 more
Pittsfield · Affordable Bike Repair at The Funky Phoenix
Just added
BASKET WEAVING WORKSHOP AT TAVERN AT THE A
Sun, Dec 27, 1:00 PM
Pittsfield · Tavern At The A
Just added
BASKET WEAVING WORKSHOP AT TAVERN AT THE A
Sun, Dec 27, 1:00 PM
Pittsfield · Tavern At The A
WERQshires presents: A DRAG Christmas Story!
Fri, Dec 4, 7:30 PM
West Stockbridge · The Foundry West Stockbridge
WERQshires presents: A DRAG Christmas Story!
Fri, Dec 4, 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Desperately Seeking The Exit
Sat, Nov 14, 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Desperately Seeking The Exit
Sat, Nov 14, 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Q-MoB Queer Men's Coffee Klatch @ #6 Depot (West Stockbridge, MA)
Sun, Nov 15, 10:00 AM + 4 more
West Stockbridge · 6 Depot St
Q-MoB Queer Men's Coffee Klatch @ #6 Depot (West Stockbridge, MA)
Sun, Nov 15, 10:00 AM + 4 more
West Stockbridge · 6 Depot St
Pro Wrestling returns to Bennington VT for Toys for Tots 11/28/26
Sat, Nov 28, 7:00 PM
Bennington · Bennington Elks Lodge #567
Pro Wrestling returns to Bennington VT for Toys for Tots 11/28/26
Sat, Nov 28, 7:00 PM
Bennington · Bennington Elks Lodge #567

1 of 224

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 Holyoke

Things to do in Hudson

Things to do in Agawam Town

Things to do in Tariffville

Things to do in Northampton

Things to do in Westfield

Things to do in Amherst Center

Trends in Cheshire

Explore more trends

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:

Wisdom Lodge Harvest Night at Hill Top Orchards

BRING IN 2027 AT THE VENUE

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:

Wacky Williamstown, MA Scavenger Hunt

Berkshire Inclusive Crafting Group @ Funky Phoenix (Pittsfield, MA)

Pride Night w/ DJ PupDaddy @ Hot Plate Brewing (Pittsfield, MA)

Penny Arcade: Longing Lasts Longer

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