Downtown Pittsfield Western Massachusetts The Berkshires

Festive Frolic: Free Hot Chocolate and Photo Ops with the Grinch
2025-12-05 17:00 - 20:00 (America/New_York) | 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.

Festive Frolic: Free Drop-in Crafts at The Berkshire Athenaeum
2025-12-06 12:00 - 15:30 | Berkshire Athenaeum, 1 Wendell Avenue, Pittsfield, MA, 01201
The Berkshire Athenaeum, Pittsfield’s Public Library, 1 Wendell Avenue, will offer free drop-in activities for all ages from 12:30 to 3 pm on Saturday, December 6. The Children’s Library will host a fun winter craft, the Young Adult Department will offer a button-making craft, and there will be festive bookmark making for adults and teens in the Blake Room.

Free Ride Day at The Berkshire Carousel
2025-12-06 12:00 - 17:00 | The Berkshire Carousel, 50 Center Street, Pittsfield, MA, 01201, United States
It’s Donkey Day on Saturday, December 6! There will be free rides in celebration of Missy the Donkey sponsored by author Kevin O’ Hara. Kevin will introduce and sign his latest book, “A Christmas Journey, Volume Two”, and there will be a special dance performance by the Scoil Rince Breifne O Ruairc Dancers at 2 pm.

Festive Frolic: Kids’ Paint & Sip
2025-12-06 12:30 - 15:00 | 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 Saturday, December 6, 12:30 to 3 pm, in the auditorium at St. Stephen’s Episcopal Church, 67 East Street.
This free holiday-themed Paint & Sip is best suited for ages 5 to 12, although younger and older children are welcome. All materials, snacks, and juice will be provided. Children will be provided with a small canvas and wooden ornament for painting.
The Berkshire Museum will be joining in on the fun with a free yarn snowflake ornament craft.
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.
This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

Festive Frolic: Photo Ops with Santa
2025-12-06 12:30 - 15:00 | Dunham Mall, 100 North Street
NOW INSIDE!! Downtown Pittsfield, Inc. will host Photo Ops with Santa on Saturday, December 6, 12:30 to 3 pm, inside Hand Crafted at 26 Dunham Mall.
Santa will be welcoming children and families to visit with him and take photos. Please bring your own camera or cell phone to capture your own photos of this special moment. There will not be a photographer on site.
Hand Crafted will be handing out free hot chocolate and cider to all in attendance, and Downtown Pittsfield, Inc. will be handing out free Winston Ornaments while supplies last.
Berkshire Community Action Council, Inc. (BCAC) invites you to help support the Elf Children’s Warm Clothing Program by bringing a NEW winter coat or pair of boots for a child in need. If you do, you’ll earn an entry into a raffle to win a luxurious one-night stay at Hotel on North.
BCAC will also be giving away free cookies to all. The raffle drawing will be at 3 pm. You do not need to be present to win.
Hand Crafted will also host “Reading with Rebel” from 12:30 to 3 pm. Drag queen, Miz Rebel Progress, has teamed up with Hand Crafted to promote literacy at this holiday storytelling event. All children who attend will leave with a free book.

This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

“Reading with Rebel” at Hand Crafted (Festive Frolic)
2025-12-06 12:30 - 15:00 | Hand Crafted, 26 Dunham Mall, Pittsfield, MA, 01201, United States
Hand Crafted, 26 Dunham Mall, will host “Reading with Rebel” from 12:30 to 3 pm. Drag queen, Miz Rebel Progress, has teamed up with Hand Crafted to promote literacy at this holiday storytelling event. All children who attend will leave with a free book.
This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

Festive Frolic: Free DIY dried floral ornaments at SOLARIUM
2025-12-06 12:30 - 15:00 | SOLARIUM Plant Shop, 46 West Street, Pittsfield, MA, 01201, United States
SOLARIUM Plant Shop, 46 West Street, invites children to drop-in to make free dried floral ornaments from 12:30 to 3 pm on Saturday, December 6.

“Reading with Rebel” at Hand Crafted
2025-12-06 12:30 - 15:00 | Hand Crafted, 26 Dunham Mall, Pittsfield, MA, 01201, United States
Hand Crafted, 26 Dunham Mall, will host “Reading with Rebel” from 12:30 to 3 pm. Drag queen, Miz Rebel Progress, has teamed up with Hand Crafted to promote literacy at this holiday storytelling event. All children who attend will leave with a free book.

Festive Frolic: Drag Story Hour with Sativo Green at Indie Readery and Records
2025-12-06 13:00 - 14:30 | Indie Readery and Records, 314 North Street, Pittsfield, MA, 01201, United States
Indie Readery and Records, 314 North Street, and Drag Story Hour Berkshires will present a holiday-themed Drag Story Hour with Sativo Green from 1 to 2:30 pm on Saturday, December 6.
