What's on in Pittsfield for free?
13 upcoming events
We've rounded up 13 upcoming events in Pittsfield for free — concerts, parties, theatre, exhibitions, family outings — updated every day. Pick a theme or just scroll.
Events in Pittsfield for free
Thu29
Today
Sat31
Saturday 31 October
Later
Thu 5 · 4 PM$0
LGBTQ+Street party
Berkshire LGBTQ+ Community Potluck @ Wander Berkshires
WANDER Berkshires
Mon 9 · 11:30 AMFree
Talk
RHTP Information & Listening Session - Pittsfield/Central Berkshires
Berkshire Innovation Center
Thu 12 · 10 AMFree
Fall Vendor Show in the Berkshires
Country Club of Pittsfield - Berkshires
Sat 14 · 9 AMFree
2026 Pittsfield Holiday Farmers Market
Zion Lutheran Church
Sat 14 · 10:30 AMFree
MiniaturesTournament
BERKSHIRE BATTLEGROUNDS RTT
Storefront
Sun 29 Nov · 11 AM$0
Q-MoB Queer Men's DND Roleplaying Adventure Group @ Wander (Pittsfield, MA)
WANDER Berkshires
Sat 12 Dec · 9 AMFree
2026 Pittsfield Holiday Farmers Market
Zion Lutheran Church
Sat 9 Jan · 9 AMFree
2027 Pittsfield Winter Farmers Market
Zion Lutheran Church
Sat 13 Feb · 9 AMFree
2027 Pittsfield Winter Indoor Farmers Market
Zion Lutheran Church
Sat 13 Mar · 9 AMFree
2027 Pittsfield Farmers Market
Zion Lutheran Church
Sat 10 Apr · 9 AMFree
2027 Pittsfield Spring Farmers Market
Zion Lutheran Church
See also in Pittsfield for free
Sat 31 · 8 PM$23.18
Concert
Halloween With Skeeter Creek At The Proprietor’s Lodge
22 Waubeek Rd, Pittsfield
Tomorrow · 7:30 PM$25–30
RockConcert
Shooting Star
The Stationery Factory, Dalton
Fri 6 · 7:30 PM$30
RockBlues
Thunderbeard: A Tribute to ZZ Top
Colonial Theatre - Pittsfield
Sat 21 · 2 PM$15–25
Singer-songwriterPop
The Little Mermen & The Princess Pals: Disney Sing Along The Ultimate Disney Tribute Band
Colonial Theater, Pittsfield
At 7:30 PM$20–40
World musicFolk / Acoustic
Andrew Wells-Oberegger Trio
The Foundry, West Stockbridge
Tomorrow · 7 PM$35
JazzConcert
TLI Close to Home: Andy Wrba & Friends
Linde Center for Music and Learning, Lenox
Sun 1 · 3 PM$40
ClassicalConcert
West Stockbridge Chamber Players Harvest Concert
West Stockbridge Historical Society
Sun 1 · 2 PMFree
ClassicalConcert
Berkshire Chamber Players Concert – 250th Anniversary Celebration of the United States of America
Stockbridge Library
Mon 2 · 6:30 PMFree
ClassicalConcert
Fabio Mittino & Bert Lams play the music of Thomas De Hartmann
Images Cinema Lounge, Williamstown
At 8 PM$12.51
KaraokeDJ set
WANDER Halloween Party
WANDER Berkshires, Pittsfield
Sat 31 · 8 PM$23.61
DJ set
The Shining @ Holiday Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Wed 4 · 7 PM$28.52
Street party
A Night Out in Pittsfield | Dinner with New Friends: Small Town Edition
Restaurant of the Week, Pittsfield
Sat 21 · 1:15 PM
Village danceSocials
Lenox Contra Dance
Lenox Community Center
Tomorrow · 6 PM$101.31
FoodMagic
The House Remembers An Immersive Halloween Dinner at The Inn at Stockbridge
The Inn at Stockbridge
Sat 31 · 7 PM$25–30
Parties
The Witch's Hallow Halloween Ball
The Stationery Factory, Dalton
Thu 12 · 7:30 PM$23.18
Stand-upComedy
Antimony Brewing Comedy Series w/ Nick Griffin
Antimony Brewing - Craft Brewery & Kitchen, Lenox
At 2 PM$56
Theatre
Mainstage Performance: CAMP SIEGFRIED
Elayne P. Bernstein Theatre, Lenox
Sun 1 · 5 PMFree
TheatreFeminism
Shakespeare & Company Presents Select Works from Women+ On The Edge of Democracy
Shakespeare & Company, Lenox
At 7 PM$50
TheatreClassical
Summer, 1976
The Unicorn Theatre, Stockbridge
Tomorrow · 7 PM$20–69
ContemporaryClassical
Ballet Nepantla’s Mística – SOLD OUT
MASS MoCA, North Adams
Tomorrow · 7 PM
ClassicalShows
Ballet Nepantla
MASS MoCA, North Adams
At 8 PM
Cinema
The Rocky Horror Picture Show Screening
Sydelle and Lee Blatt Performing Arts Center, Pittsfield
At 8 PM$25
Cinema
The Rocky Horror Picture Show Screening at BSC
30 Union Street, Pittsfield, MA 01201
At 1 PM
Literature
October Book Discussion: Myskania by Richard Matturro
Dalton Free Public Library
At 9 AM
ExhibitionDisability
Roots, Stems, Leaves, Sky: Exhibit at Mass Audubon Pleasant Valley Wildlife Sanctuary
Mass Audubon's Pleasant Valley Wildlife Sanctuary, Lenox
At 6 PM$20
FoodTalk
Beyond Riesling: Discovering German Wine
Dare Bottleshop & Provisions, Lenox
Sat 31 · 3 PM$30
FoodHeritage
Afternoon High Tea at the Susan B. Anthony Birthplace Museum
Susan B. Anthony Birthplace Museum, Adams
Sun 1 · 12 PMFree
FoodStreet party
Lenox Restaurant Week
Lenox, Massachusetts
Tue 3 · 1 PM
Literature
November 2026 Book Club
Lenox Library
Fri 6 · 7 PM$20–25
LiteratureTalk
The Lit Salon | An Evening with Author Marcia Chatelain Accompanied by Singer-Songwriter Chantell McCulloch
The Mount
Fri 6 · 7 PM
LiteratureTalk
Author Talk with Heather A. Campbell
West Stockbridge Town Offices
Fri 13 · 11 AM
Crafts
Holiday Arts and Crafts Fair
Kimball Farms, Lenox
At 1 PM
Guided tour
Guided Tour at the Lee Library
Lee Library
Fri 6
ExhibitionOpening
The Art of Resistance
MCLA Gallery 51, North Adams
Tomorrow · 5 PMFree
Literature
Book Launch - Alice Sees Ghosts by Daisy Rockwell
The Red Lion Inn, Stockbridge
Tue 3 · 1:30 PM
Literature
Book Club - “Being Mortal”
Becket Athenaeum
Your passions nearby
Tap what you're into — we'll find the outings around you.
Venues in Pittsfield for free
WANDER Berkshires
3 events
WANDER
2 events
Zion Lutheran Church
6 events
Sydelle and Lee Blatt Performing Arts Center
2 events
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Berkshire Athenaeum, Pittsfield's Public Library
10 events
Berkshire Museum
5 events
First Baptist Church
9 events
Colonial Theatre - Pittsfield
7 events
Colonial Theater
7 events
Storefront
2 events
22 Waubeek Rd
2 events