Events and Things to do in Cheshire, MA

Search for something you love or check out popular events in your area.

Going fast
Let's Get Real Conference 2026
Fri, Jun 26, 8:00 AM
Pittsfield · Berkshire Community College
Going fast
Let's Get Real Conference 2026
Fri, Jun 26, 8:00 AM
Pittsfield · Berkshire Community College
Going fast
IAN MAKSIN in PITTSFIELD, MA: "CELLO FOR PEACE" Concert Tour
Thu, May 28, 7:30 PM
Pittsfield · Sanctum Gallery
Going fast
IAN MAKSIN in PITTSFIELD, MA: "CELLO FOR PEACE" Concert Tour
Thu, May 28, 7:30 PM
Pittsfield · Sanctum Gallery
PAINT & SIP
Fri, Jun 5, 6:00 PM
Pittsfield · Tavern At The A
PAINT & SIP
Fri, Jun 5, 6:00 PM
Pittsfield · Tavern At The A
Rumpy's Returns: One Night Only!
Sat, Jun 6, 5:00 PM
Lenox · Belvedere Lenox Event Space
Rumpy's Returns: One Night Only!
Sat, Jun 6, 5:00 PM
Lenox · Belvedere Lenox Event Space
Sales end soon
LGBTQ Spring Tuneup Bike Ride on Ashuwillticook Rail Trail (Cheshire, MA)
Saturday at 2:00 PM
Cheshire · 329 S State Rd
Sales end soon
LGBTQ Spring Tuneup Bike Ride on Ashuwillticook Rail Trail (Cheshire, MA)
Saturday at 2:00 PM
Cheshire · 329 S State Rd
Carla Cooke at the Worthington Golf Club - May 30th Concert!
Sat, May 30, 7:00 PM
Worthington · The Links at Worthington
Carla Cooke at the Worthington Golf Club - May 30th Concert!
Sat, May 30, 7:00 PM
Worthington · The Links at Worthington
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Jun 13, 7:30 PM
North Adams · Bright Ideas Brewing
Comedy On Tap at Bright Ideas Brewing in North Adams, MA!
Sat, Jun 13, 7:30 PM
North Adams · Bright Ideas Brewing
PAINT & SIP
Thu, Jun 18, 6:00 PM
Lanesborough · The Venue At Skyline
PAINT & SIP
Thu, Jun 18, 6:00 PM
Lanesborough · The Venue At Skyline
Sales end soon
Q-MoB Board & Leadership Team Monthly Meeting (Pittsfield, MA)
Tuesday at 7:00 PM + 19 more
Pittsfield · 110 South St
Sales end soon
Q-MoB Board & Leadership Team Monthly Meeting (Pittsfield, MA)
Tuesday at 7:00 PM + 19 more
Pittsfield · 110 South St
Sales end soon
Lean Six Sigma Green Belt (LSSGB) Certification Training in Pittsfield, MA
Tuesday at 9:00 AM
Pittsfield, MA · Pittsfield, MA
Sales end soon
Lean Six Sigma Green Belt (LSSGB) Certification Training in Pittsfield, MA
Tuesday at 9:00 AM
Pittsfield, MA · Pittsfield, MA
PMP Certification 4 Days Classroom Training in Pittsfield, MA
Tuesday at 9:00 AM
Pittsfield, MA · Pittsfield, MA
PMP Certification 4 Days Classroom Training in Pittsfield, MA
Tuesday at 9:00 AM
Pittsfield, MA · Pittsfield, MA
Agile and Scrum Certification Training in Pittsfield, MA
Tomorrow at 9:00 AM + 7 more
Pittsfield · Pittsfield, MA
Agile and Scrum Certification Training in Pittsfield, MA
Tomorrow at 9:00 AM + 7 more
Pittsfield · Pittsfield, MA
Sales end soon
PMP (Project Management) Certification Training in Pittsfield, MA
Tuesday at 9:00 AM + 7 more
Pittsfield · Regus Business Center
Sales end soon
PMP (Project Management) Certification Training in Pittsfield, MA
Tuesday at 9:00 AM + 7 more
Pittsfield · Regus Business Center
Data Analytics Certification Training in Pittsfield, MA
Wednesday at 9:00 AM + 6 more
Pittsfield · Pittsfield, MA
Data Analytics Certification Training in Pittsfield, MA
Wednesday at 9:00 AM + 6 more
Pittsfield · Pittsfield, MA
Vyntyge Skynyrd at Worthington Golf Club: June 27th
Sat, Jun 27, 6:30 PM
Worthington · The Links at Worthington
Vyntyge Skynyrd at Worthington Golf Club: June 27th
Sat, Jun 27, 6:30 PM
Worthington · The Links at Worthington
Pride Night w/ DJ PupDaddy @ Hot Plate Brewing (Pittsfield, MA)
Thu, Jun 4, 7:00 PM + 3 more
Pittsfield · Hot Plate Brewing Co.
Pride Night w/ DJ PupDaddy @ Hot Plate Brewing (Pittsfield, MA)
Thu, Jun 4, 7:00 PM + 3 more
Pittsfield · Hot Plate Brewing Co.
The Revival House Wine Parlor + Bites
Fri, Jun 5, 5:30 PM + 55 more
Adams · 17 Commercial St
The Revival House Wine Parlor + Bites
Fri, Jun 5, 5:30 PM + 55 more
Adams · 17 Commercial St
A Night Out in Pittsfield | Dinner with New Friends: Small Town Edition
Thu, Jun 4, 7:00 PM + 6 more
Pittsfield · Restaurant of the Week
A Night Out in Pittsfield | Dinner with New Friends: Small Town Edition
Thu, Jun 4, 7:00 PM + 6 more
Pittsfield · Restaurant of the Week
PMP Certification In-Person Training in Pittsfield, MA
Tue, Jun 9, 9:00 AM
Pittsfield · 437 North St
PMP Certification In-Person Training in Pittsfield, MA
Tue, Jun 9, 9:00 AM
Pittsfield · 437 North St

Trends in Cheshire

Explore more trends

Frequently asked questions about Cheshire

What are the best events to attend?

According to Eventbrite, the best events are:

Let's Get Real Conference 2026

IAN MAKSIN in PITTSFIELD, MA: "CELLO FOR PEACE" Concert Tour

PAINT & SIP

Rumpy's Returns: One Night Only!

Which events are currently trending in Cheshire?

The trending searches this month in Cheshire are:

winter holiday

Which events are coming up?

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

Agile and Scrum Certification Training in Pittsfield, MA

LGBTQ Spring Tuneup Bike Ride on Ashuwillticook Rail Trail (Cheshire, MA)

Lean Six Sigma Green Belt (LSSGB) Certification Training in Pittsfield, MA

PMP Certification 4 Days Classroom Training in Pittsfield, MA

Let's Get Real Conference 2026

Let's Get Real Conference 2026

IAN MAKSIN in PITTSFIELD, MA: "CELLO FOR PEACE" Concert Tour

IAN MAKSIN in PITTSFIELD, MA: "CELLO FOR PEACE" Concert Tour

PAINT & SIP

PAINT & SIP

Rumpy's Returns: One Night Only!

Rumpy's Returns: One Night Only!

LGBTQ Spring Tuneup Bike Ride on Ashuwillticook Rail Trail (Cheshire, MA)

LGBTQ Spring Tuneup Bike Ride on Ashuwillticook Rail Trail (Cheshire, MA)

Carla Cooke at the Worthington Golf Club - May 30th Concert!

Carla Cooke at the Worthington Golf Club - May 30th Concert!

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

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

PAINT & SIP

PAINT & SIP

Q-MoB Board & Leadership Team Monthly Meeting (Pittsfield, MA)

Q-MoB Board & Leadership Team Monthly Meeting (Pittsfield, MA)

Lean Six Sigma Green Belt (LSSGB) Certification Training in Pittsfield, MA

Lean Six Sigma Green Belt (LSSGB) Certification Training in Pittsfield, MA

PMP Certification 4 Days Classroom Training in Pittsfield, MA

PMP Certification 4 Days Classroom Training in Pittsfield, MA

Agile and Scrum Certification Training in Pittsfield, MA

Agile and Scrum Certification Training in Pittsfield, MA

PMP (Project Management) Certification Training in Pittsfield, MA

PMP (Project Management) Certification Training in Pittsfield, MA

Data Analytics Certification Training in Pittsfield, MA

Data Analytics Certification Training in Pittsfield, MA

Vyntyge Skynyrd at Worthington Golf Club: June 27th

Vyntyge Skynyrd at Worthington Golf Club: June 27th

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

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

The Revival House Wine Parlor + Bites

The Revival House Wine Parlor + Bites

A Night Out in Pittsfield | Dinner with New Friends: Small Town Edition

A Night Out in Pittsfield | Dinner with New Friends: Small Town Edition

PMP Certification In-Person Training in Pittsfield, MA

PMP Certification In-Person Training in Pittsfield, MA

Things to do around Cheshire

Trends in Cheshire

1. Winter holiday

What are the best events to attend?

Which events are currently trending in Cheshire?

Which events are coming up?