Downtown Pittsfield Western Massachusetts The Berkshires

Festive Frolic: The Berkshire Bazaar at The Holiday Inn
2025-12-06 11:00 - 16:00 (America/New_York) | The Holiday Inn & Suites, 1 West Street, Pittsfield, MA, 01201, United States
The Festive Frolic continues Saturday, December 6, with The Berkshire Bazaar hosted by Thistle ‘n Thorn Floral at The Holiday Inn, 1 West Street, from 11 am to 4 pm. Shop handmade goods and thoughtful gifts from dozens of local makers, artists, and small businesses.
Enjoy a complimentary cocoa bar (while supplies last!), free photo station, and complimentary face painting — fun for all ages!
Enter through the main hotel entrance, then take the elevators or stairs to the first floor, where you’ll find the grand ballroom.

Festive Frolic: Park Square Tree Lighting Ceremony
2025-12-05 17:30 - 18:30 | Park Square
The City of Pittsfield’s Park Square Tree Lighting Ceremony will be on Friday, December 5 starting at 6 pm. Join Santa, Mrs. Claus, and the City of Pittsfield’s Recreation Department for this festive holiday tradition. The Pittsfield High School Chorus will perform a variety of carols around 5:45 pm before the ceremony begins, and Santa and Mrs. Claus will arrive following the tree lighting. Lipton Market will be providing free hot chocolate and coffee in Park Square during the event.
Those planning to attend the ceremony are asked to bring non-perishable food items that will be donated to the Christian Center’s food pantry.
Artists Peter Vacchina and Robert Markey will be creating holiday-themed ice sculptures in Park Square beginning at 5 pm. Their live ice sculpting will continue throughout the evening for attendees to watch, subject to favorable weather conditions.
This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

Festive Frolic: Free Hot Chocolate and Photo Ops with the Grinch
2025-12-05 17:00 - 20:00 | Otto’s Kitchen & Comfort, 95 East Street, Pittsfield, MA, 01201, United States
Otto’s Kitchen & Comfort, 95 East Street, will be providing free hot chocolate and photo ops with the Grinch from 5 to 8 pm on Friday, December 5.
Stop by before or after the Park Square Tree Lighting Ceremony!
This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

XWA Superstars of Wrestling return to Pittsfield
2025-11-22 17:00 - 19:00 | Masonic Temple, 116 South Street, Pittsfield, MA, 01201, United States
Get ready, Pittsfield! XWA Wrestling is back with another night of high-impact, family-friendly action you won’t want to miss!
Advance Ticket Special:
Kids 10 & under – ONLY $10
Adults – ONLY $15
All tickets are $25 at the door. Buy early and save! All tickets are General Admission seating. Sit where you like – first come first serve!
Buy tickets online at XWATIX.COM or at the entrance (while seats last).
Concession Stand available! Meet & Greet with the wrestlers during intermission!

Bell Time 5 pm
Doors open at 4:30 pm

Wandering Dance Festival: November 9-15
2025-11-09 - 2025-11-15 | MA
Festival attendees can take part in free workshops, learn from esteemed choreographers, and showcase their own talents during open dance sessions. Stay tuned to milltownfoundation.org/wandering-dance-festival for more information!

Free Kids’ Harvest Paint & Sip
2025-11-07 17:00 - 19:00 | St. Stephen’s Episcopal Church, 67 East Street, Pittsfield, MA, 01201, United States
Downtown Pittsfield, Inc. and St. Stephen’s Episcopal Church will host a Free Kids’ Paint & Sip on Friday, November 7, from 5 to 7 pm, in the auditorium at St. Stephen’s Episcopal Church, 67 East Street.
This free Harvest-themed Paint & Sip is best suited for ages 5 to 12, although younger and older children are welcome. All materials, instruction, snacks, and juice will be provided. Children are welcome to drop in anytime over the course of the event, and all children must be accompanied by an adult. The auditorium is on the second floor of the parish house, and the entrance is on Allen Street.

Depot After Dark: Teen Dance Party Edition!
2025-10-18 19:00 - 21:30 | 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 7 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 | 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.
