Discover Wander Berkshires Events & Activities in Pittsfield, MA

Great Barrington Bash Scavenger Hunt
Today at 11:00 AM + 437 more
Patisserie Lenox
Great Barrington Bash Scavenger Hunt
Today at 11:00 AM + 437 more
Patisserie Lenox
Honor First Nations Gathering
Fri, Aug 8, 7:00 PM
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Honor First Nations Gathering
Fri, Aug 8, 7:00 PM
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holyoke Preservation Trust's 5th Annual Garden Tour
Sat, Jun 28, 8:30 AM
Holyoke Preservation Trust
Holyoke Preservation Trust's 5th Annual Garden Tour
Sat, Jun 28, 8:30 AM
Holyoke Preservation Trust
SURVIVAL CENTER BENEFIT - with Donnie Gallagher & Friends
Wed, Jun 4, 7:00 PM
The Drake
SURVIVAL CENTER BENEFIT - with Donnie Gallagher & Friends
Wed, Jun 4, 7:00 PM
The Drake
Light Up The World Book Tour Pittsfield PRIDE Signing at Barnes & Noble
Sat, Jun 7, 5:00 PM
Barnes & Noble
Light Up The World Book Tour Pittsfield PRIDE Signing at Barnes & Noble
Sat, Jun 7, 5:00 PM
Barnes & Noble
Sales end soon
Site Visit: Forge Project Collection & Exhibition Programs
Friday at 10:00 AM
Taghkanic
Sales end soon
Site Visit: Forge Project Collection & Exhibition Programs
Friday at 10:00 AM
Taghkanic
The Flutter Express Round-Trip New York City Service
Tue, Jun 3, 6:00 AM
Yankee Trails
The Flutter Express Round-Trip New York City Service
Tue, Jun 3, 6:00 AM
Yankee Trails
Q-MoB NEW Queer Men's Coffee Klatch @ W Collective Coffee (Bennington, VT)
Sun, May 25, 10:00 AM + 8 more
W. Collective
Q-MoB NEW Queer Men's Coffee Klatch @ W Collective Coffee (Bennington, VT)
Sun, May 25, 10:00 AM + 8 more
W. Collective
Site Visit: Forge Project Land Remediation & Research Programs
Fri, Jun 13, 2:00 PM
Taghkanic
Site Visit: Forge Project Land Remediation & Research Programs
Fri, Jun 13, 2:00 PM
Taghkanic
Sales end soon
Chatham - Planning Ahead: Wills, Trusts & Peace of Mind
Thursday at 6:00 PM
29 Hudson Ave
Sales end soon
Chatham - Planning Ahead: Wills, Trusts & Peace of Mind
Thursday at 6:00 PM
29 Hudson Ave
HBJ's 2025 Family Business Awards Presented By: Berkshire Bank
Thu, Jun 12, 5:00 PM
Farmington Gardens
HBJ's 2025 Family Business Awards Presented By: Berkshire Bank
Thu, Jun 12, 5:00 PM
Farmington Gardens
NEW Queer Men's Intergenerational Mentoring Team (Pittsfield, MA)
Tomorrow at 6:30 PM + 1 more
Berkshire Athenaeum, Pittsfield's Public Library
NEW Queer Men's Intergenerational Mentoring Team (Pittsfield, MA)
Tomorrow at 6:30 PM + 1 more
Berkshire Athenaeum, Pittsfield's Public Library
Nutty Northampton, MA Scavenger Hunt
Today at 11:00 AM + 409 more
Share Coffee Northampton
Nutty Northampton, MA Scavenger Hunt
Today at 11:00 AM + 409 more
Share Coffee Northampton
Paint Your Pet
Tomorrow at 6:00 PM
Locker Room Sports Pub
Paint Your Pet
Tomorrow at 6:00 PM
Locker Room Sports Pub
Q-MoB NEW Queer Sci Fi/Fantasy Book Club (Pittsfield, MA)
Thu, May 22, 6:00 PM + 5 more
Hot Plate Brewing Co.
Q-MoB NEW Queer Sci Fi/Fantasy Book Club (Pittsfield, MA)
Thu, May 22, 6:00 PM + 5 more
Hot Plate Brewing Co.
Nutty Northampton, MA Amazing Race & Tour
Today at 11:00 AM + 437 more
Share Coffee Northampton
Nutty Northampton, MA Amazing Race & Tour
Today at 11:00 AM + 437 more
Share Coffee Northampton
Summer Reading Rep Picks
Wed, Jun 25, 7:00 PM
Odyssey Bookshop
Summer Reading Rep Picks
Wed, Jun 25, 7:00 PM
Odyssey Bookshop
NEW Queer Men's D&D Roleplaying Group @ UCC Pittsfield (Pittsfield, MA)
Sun, May 25, 2:00 PM + 13 more
110 South St
NEW Queer Men's D&D Roleplaying Group @ UCC Pittsfield (Pittsfield, MA)
Sun, May 25, 2:00 PM + 13 more
110 South St
Men's Retreat
Fri, Jul 25, 6:00 PM
Mount Snow Resort
Men's Retreat
Fri, Jul 25, 6:00 PM
Mount Snow Resort

Great Barrington Bash Scavenger Hunt

Great Barrington Bash Scavenger Hunt

Honor First Nations Gathering

Honor First Nations Gathering

Holyoke Preservation Trust's 5th Annual Garden Tour

Holyoke Preservation Trust's 5th Annual Garden Tour

SURVIVAL CENTER BENEFIT - with Donnie Gallagher & Friends

SURVIVAL CENTER BENEFIT - with Donnie Gallagher & Friends

Light Up The World Book Tour Pittsfield PRIDE Signing at Barnes & Noble

Light Up The World Book Tour Pittsfield PRIDE Signing at Barnes & Noble

Site Visit: Forge Project Collection & Exhibition Programs

Site Visit: Forge Project Collection & Exhibition Programs

The Flutter Express Round-Trip New York City Service

The Flutter Express Round-Trip New York City Service

Q-MoB NEW Queer Men's Coffee Klatch @ W Collective Coffee (Bennington, VT)

Q-MoB NEW Queer Men's Coffee Klatch @ W Collective Coffee (Bennington, VT)

Site Visit: Forge Project Land Remediation & Research Programs

Site Visit: Forge Project Land Remediation & Research Programs

Chatham - Planning Ahead: Wills, Trusts & Peace of Mind

Chatham - Planning Ahead: Wills, Trusts & Peace of Mind

HBJ's 2025 Family Business Awards Presented By: Berkshire Bank

HBJ's 2025 Family Business Awards Presented By: Berkshire Bank

NEW Queer Men's Intergenerational Mentoring Team (Pittsfield, MA)

NEW Queer Men's Intergenerational Mentoring Team (Pittsfield, MA)

Nutty Northampton, MA Scavenger Hunt

Nutty Northampton, MA Scavenger Hunt

Paint Your Pet

Paint Your Pet

Q-MoB NEW Queer Sci Fi/Fantasy Book Club (Pittsfield, MA)

Q-MoB NEW Queer Sci Fi/Fantasy Book Club (Pittsfield, MA)

Nutty Northampton, MA Amazing Race & Tour

Nutty Northampton, MA Amazing Race & Tour

Summer Reading Rep Picks

Summer Reading Rep Picks

NEW Queer Men's D&D Roleplaying Group @ UCC Pittsfield (Pittsfield, MA)

NEW Queer Men's D&D Roleplaying Group @ UCC Pittsfield (Pittsfield, MA)

Men's Retreat

Men's Retreat

Things to do around Pittsfield

Trends in Pittsfield

1. Craft fairs

2. Easter brunch

3. Stand up comedy

4. Easter egg hunt

5. Mothers day brunch

6. Music bingo berkshire

7. Paint and sip

8. Speed dating

9. Dance events

10. Open mic

11. Singles events

12. Live music