Downtown Pittsfield Western Massachusetts The Berkshires

Depot After Dark: Teen Dance Party Edition!
2025-10-18 19:00 - 21:30 (America/New_York) | Liberty Street, Liberty Street, Pittsfield, MA, 01201, United States
Depot After Dark: Teen Dance Party Edition! will be held on Saturday, October 18, 7 to 9:30 pm, on Liberty Street (the alleyway between Tito’s/Wander and Crawford Square).
Depot After Dark: Teen Dance Party Edition! is open to Berkshire County high school students only, and attendees must have a current, valid high school ID.
This event is a collaboration between Downtown Pittsfield, Inc. and Wander Berkshires. There will be a live DJ, and VonBowtie Face Painting will be offering free glitter and glow face paint. Halloween costumes are encouraged but not required. Please do not wear masks. There will be beverages available for purchase from Wander; and Downtown Pittsfield, Inc. will be providing adult chaperones to ensure a safe and supportive environment.
Depot After Dark: Teen Dance Party Edition is presented by Downtown Pittsfield, Inc. in partnership with Mill Town Foundation, the City of Pittsfield, and WANDER Berkshires.
For more information on Downtown Pittsfield… It’s Alive!, call Downtown Pittsfield, Inc. at 413-443-6501.

Night Circus: Free Tarot Readings with Emily Dunsay Wild
2025-10-18 15:00 - 18:00 | 90 North Studio, 90 North Street, Pittsfield, MA, 01201, United States
Enjoy free 3 Card Tarot Readings with master psychic, alchemist, life coach, and poet Emily Dunsay Wild inside 90 North Studio (90 North Street). The readings are free, but tips are appreciated.
“My methods are vast, I am a channel for nature magic, spirit realms, angelic messages, beauty, art, inspiration, sacred ceremony, expert tarot oracle interpretation,” says Emily. “My specialties, seeing the past present & future. Releasing trauma & psychic wounds. Creating breathtaking original spells & manifesting what your heart truly yearns for. I use a plentitude of skills & tools woven in a master tapestry to give each client the most accurate & thorough transformation possible of body mind & soul. My clients include celebrities, fellow master healers & everyone else in between.” Learn more about Emily at thejewelsofknowing.com.

Downtown Pittsfield… It’s Alive! Night Circus
2025-10-18 15:00 - 18:00 | Dunham Mall, 100 North Street
Downtown Pittsfield… It’s Alive! Night Circus: Saturday, October 18, 3 to 6 pm, on Dunham Mall, School Street, and the portion of North Street that connects the two.
The Downtown Pittsfield… It’s Alive! Night Circus will feature live ska and punk rock bands presented by 413ska; a fire show with Last Ember; free Tarot Readings by Emily Dunsay Wild at 90 North Studio; a beer garden with Hot Plate Brewing Co.; specialty alcoholic beverages from HAND CRAFTED Catering; food from Flavourful Bites, HAND CRAFTED Catering, and Cookie’s Cupcakes; and vendors curated by Jake Seeley of Bomb Shack Vintage.
Last Ember will bring two fire performances to School Street at 4 and 5 pm!
Jesse M. Thomas (Last Ember) has dedicated much of his life to the mastery of prop manipulation and fire-spinning. Jesse has a variety of 10+ acts (from flaming staves to fire eating to knife juggling) and over 15 years professional training.
413ska will present 3 bands on Dunham Mall.
CARSON DALY CITY TRAIN (3 to 4 pm):
A supergroup featuring members of Futon Lasagna, The Agonizers, ghost tones, So Many Dangers, and Steppin Razor Blades – playing covers from the Carson Daly TRL era and your favorite punk songs from the 90’s!
Datura (4:15 to 5 pm):
Datura is a Punk Rock Band from Pittsfield with Lead singer and rhythm guitarist Paxton miller, Lead guitarist Zach Farina, Drummer Brody Barnes, and semi temporary Bassist Jack Bradway. Datura’s style is inspired by Greenday, blink-182, The Ramones, and other punk classics, attempting to provide a comical, fun experience and music an audience can relate to.
HardCar (5:15 to 6 pm):
HardCar is a four-piece alternative punk rock band from Western MA. They combine elements of The Ramones, The Vandals, and The Muppets to create a frenetic cartoon fight cloud of three chord mischief with more catchy hooks than a fishing derby. They released the EP, “Cars of Hardness” in 2024.
The band schedule is subject to change.
Enjoy free 3 Card Tarot Readings with master psychic, alchemist, life coach, and poet Emily Dunsay Wild inside 90 North Studio (90 North Street). The readings are free, but tips are appreciated.
“My methods are vast, I am a channel for nature magic, spirit realms, angelic messages, beauty, art, inspiration, sacred ceremony, expert tarot oracle interpretation,” says Emily. “My specialties, seeing the past present & future. Releasing trauma & psychic wounds. Creating breathtaking original spells & manifesting what your heart truly yearns for. I use a plentitude of skills & tools woven in a master tapestry to give each client the most accurate & thorough transformation possible of body mind & soul. My clients include celebrities, fellow master healers & everyone else in between.” Learn more about Emily at thejewelsofknowing.com.
Downtown Pittsfield… It’s Alive! Night Circus is presented by Downtown Pittsfield, Inc. in partnership with Mill Town Foundation, the City of Pittsfield, Bomb Shack Vintage, 413ska, HAND CRAFTED Catering & Events, Hot Plate Brewing Co., and 90 North Studio.
For more information on Downtown Pittsfield… It’s Alive!, call Downtown Pittsfield, Inc. at 413-443-6501.

Downtown Pittsfield… It’s Alive! Kids’ Zone
2025-10-18 10:00 - 13:00 | Lawn of St. Joseph’s Church, 414 North Street, Pittsfield, MA, 01201, United States
Downtown Pittsfield… It’s Alive! Kids’ Zone: Saturday, October 18, 10 am to 1 pm
The Downtown Pittsfield… It’s Alive! Kids’ Zone will be held on the St. Joseph’s Church lawn. The Kids’ Zone will feature a bounce house, Halloween-themed arts & crafts, games, face painting, balloon twisting, giveaways, live entertainment, and more! All Kids’ Zone activities are free, and costumes are encouraged.
There will be free Face Painting and Balloon Twisting by BTC Family Entertainment (Bowey the Clown and Magic Brushes); a live DJ, and Opal Raven Cirque will perform a variety show at 11 am and 12 pm. Downtown Pittsfield, Inc. will host a Halloween Paint & Sip activity.
Berkshire Art Center will be there with a spooky ghost pull art project for all ages; and Berkshire Museum will be there with their Mobile Museum Unit and Large Dinosaur Bone Blocks for kids to make their own dinosaurs!
There will be additional free activities provided by the Berkshire Athenaeum, Berkshire County Head Start/Pittsfield CFCE, Berkshire District Attorney’s Office, Berkshire Music School, Foster MA/Adopt MA, Susan B Anthony Birthplace Museum, and The Berkshire County Kids’ Place.
Downtown Pittsfield… It’s Alive! Kids’ Zone is presented by Downtown Pittsfield, Inc. in partnership with Mill Town Foundation, the City of Pittsfield, St. Joseph’s Church, and Carr Hardware.
For more information on Downtown Pittsfield… It’s Alive!, call Downtown Pittsfield, Inc. at 413-443-6501.

The Weekend: A Stockbridge Story
2025-10-12 15:00 - 17:00, 2025-10-11 19:30 - 21:30, 2025-10-11 14:00 - 16:00, 2025-10-10 19:30 - 21:30, 2025-10-09 19:30 - 21:30, 2025-10-08 19:00 - 21:00, 2025-10-05 15:00 - 17:00, 2025-10-04 19:30 - 21:30 and 10 more dates | Barrington Stage Company, Sydelle and Lee Blatt Performing Arts Center, 36 Linden Street, Pittsfield, MA, 01201, United States
The Weekend | SEPT 16-OCT 12 | ST. GERMAIN STAGE
By BEN DISKANT
Directed by ALAN PAUL
*WORLD PREMIERE* It was a quick, romantic getaway. Just Beth and Tom… and his hopeless brother, Allan. The Weekend is a new play about fresh perspectives, missed opportunities, and finding the courage to move forward again.
Show times are as follows:*
Wednesdays: 7 pm
Thursdays: 7:30 pm
Fridays: 7:30 pm
Saturdays: 2 pm & 7:30 pm
Sundays: 3 pm
*Show times are subject to change
Click here to purchase tickets!

Pittsfield Farmers Market
2025-10-11 09:00 - 13:00, 2025-10-04 09:00 - 13:00, 2025-09-27 09:00 - 13:00 | The Common, First Street, Pittsfield, MA, 100 First Street, Pittsfield, MA, 01201, United States
Each week at the Pittsfield Farmers Market, shoppers will discover a vibrant selection of farm-fresh produce, meat, eggs, baked goods, flowers, and handcrafted items, all while enjoying live music, kids activities, and interactive experiences.
There will be a fantastic lineup of new and returning vendors, offering something for everyone—from your weekly groceries to special treats and gifts. And back by popular demand: Supersized Second Saturdays! These monthly celebrations bring extra fun with a Makers Market, chef demos, family-friendly activities, contests, and more.

Back Porch Concert: The Housie Shakers
2025-09-28 18:00 - 21:30 | Hancock Shaker Village, 1843 West Housatonic Street, Pittsfield, MA, 01201, United States
The Housie Shakers bring a variety of styles to the mix, with wide-ranging covers and original music spanning rock, blues, pop, bluegrass, reggae, Americana, and improvisational groove. They don’t take themselves too seriously and have no ambitions to go on the road (as if the 12 kids they have collectively would make that possible anyway)… they’re just out to play local gigs and give people a chance to hang out, let loose, dance, and have a good time! The band’s name is a nod to their home community and the people and places that have shaped their musical journeys.
The Housie Shakers are Simeon Bittman (drums & vocals), Noah Cook-Dubin (guitar, cavaquinho & vocals), Jonathan Denmark (guitar & vocals), and Colin Ovitsky (bass).

Annual Country Fair at Hancock Shaker Village
2025-09-28 10:00 - 17:00, 2025-09-27 10:00 - 17:00 | Hancock Shaker Village, 1843 West Housatonic Street, Pittsfield, MA, 01201, United States
Spend the weekend celebrating what makes the Berkshires special: fine artisanship, local food, breathtaking beauty, exploring the trail, and family fun. This year’s fair includes live music, workshops and demonstrations, family activities, farm animals, a farmer’s market, craft beer, antique tractors, quilt show, and dozens of craft vendors.
Included in admission/free to Hancock Shaker Village members.

Depot After Dark: Come As You Are Dance Party with DJ BFG
2025-09-26 20:00 - 23:00 | Liberty Street, Liberty Street, Pittsfield, MA, 01201, United States
Come As You Are Dance Party with DJ BFG
Friday, September 26, 8 to 11 pm
Downtown Pittsfield, Inc., Tito’s Mexican Bar & Grill, and Wander Berkshires are hosting “Depot After Dark” on select evenings this summer on Liberty Street (the alleyway between Tito’s/Wander and Crawford Square).
Beverages including beer, wine, and margaritas will be available from Tito’s, and non-alcoholic “zero proof” cocktails and other specialty drinks will be available from Wander. Attendees are invited to bring their own food or order takeout from Tito’s.
Friday, September 26: WANDER presents Come As You Are Dance Party with DJ BFG
Join us for a joyful, all-ages community dance gathering where there’s no pressure to perform—just a space to move, breathe, release, and reconnect. Come exactly as you are.
$10 Cover. Wander is always pay what you can (PWYC)!

“Pittsfield Paintbox Artist Exhibition”
2025-09-25 10:00 - 14:00 | Downtown Pittsfield, Inc., 431 North Street, Pittsfield, MA, 01201, United States
Downtown Pittsfield, Inc. and Framework will feature a brand-new “Pittsfield Paintbox Artist Exhibition” featuring 4 local artists at Framework by Downtown Pittsfield, Inc. (437 North Street).
Featured artists are Susan Gail Catelotti, Melissa Matsuki Lillie, Anastasia Drayton, and Eternity Joy Alice Williams.
The exhibition will be on view Monday through Thursday, 10 am to 2 pm, September 5 through September 25, by visiting the Downtown Pittsfield, Inc. offices at 431 North Street.
The Pittsfield Paintbox Program is a program of the City of Pittsfield’s Office of Cultural Development. The Paintbox Program celebrates local artists, enlivens the streetscape, and discourages vandalism of utility boxes throughout the downtown. Four Paintbox designs will be installed in Pittsfield this summer by the artists in this exhibition at Framework by Downtown Pittsfield, Inc.
Susan Gail Catelotti is an artist, illustrator, and graphic designer based in Peru, Massachusetts. She holds a degree in Illustration from the Rhode Island School of Design and has illustrated more than 15 children’s books for a range of authors. Her work also includes public art and mural projects all rooted in her love for storytelling through image.
Deeply inspired by the forests, wildlife, and quiet magic of the Berkshires, Susan often begins her creative process by exploring the natural world around her. Her paintings and illustrations are filled with creatures—both real and imagined—that add a sense of whimsy, weirdness, and delight to every scene. Whether she’s illustrating a picture book or painting a woodland tableau, her work invites viewers to pause, look closer, and rediscover a sense of wonder.
Melissa Matsuki Lillie is painter whose artwork references natural forms using a personal visual language of vibrant colors and complex layers to reflect on the macroscopic and microscopic world. Her paintings evoke a sense of space that has been flattened and layered, revealing strands and structures of line and color interacting fluidly with hidden landscapes. In addition to painting, she frequently works sculpturally, creating forms that celebrate both line and color.
Born in Maryland, Melissa attended the Maryland Institute College of Art where she earned a Bachelor of Fine Arts degree. She currently lives and works in the Berkshire Hills of Massachusetts.
For over two decades, Anastasia Drayton has had the privilege of working as a horticulturist in the Berkshire landscape. This time spent observing plants and ecosystems has deepened her understanding of the natural world and its connection to human-made spaces. Her work—both in horticulture and art—is rooted in yielding to nature, allowing it to shape and inspire her designs.
Watercolor plays a central role in Anastasia’s process, applied in a way that allows it to move freely across the surface – guided more by gravity and chance than by control. Anastasia works in other mediums as well, but always with a sense that she is only gently guiding the creative process. She often incorporates natural elements like branches and lichens whose forms mirror organic patterns, allowing nature to shape the composition. In this way, the human hand becomes secondary; instead, she trusts the materials and environment to create their own beauty. By letting nature guide each piece, it reminds the viewer that we don’t always need to cling so tightly—things have a way of unfolding as they’re meant to, naturally and inevitably. Anastasia finds so much resilience, hope, and peace in the natural world, and through her art, she aims to honor that connection and invite others to see the world with the same reverence.
Eternity Joy Alice Williams is currently pursuing her associate’s degree in Fine Arts at Berkshire Community College. When creating works of art, she usually likes using Prismacolor colored pencils and oil pastels, along with other materials. She’s always had a love for drawing, but recently she has had more of a focus on different vegetables and fruits. With them, she wants to display the importance of fresh produce in communities.
The gallery at Framework by Downtown Pittsfield, Inc. is funded in part by a grant from the Pittsfield Cultural Council; a local agency which is supported by the Mass Cultural Council, a state agency.
