Downtown Pittsfield Festive Frolic: Friday, December 6 and Saturday, December 7
Friday, December 6:
Tree Lighting Ceremony at Park Square
Wreath Art Auction at the Lichtenstein Center for the Arts
Hot Chocolate & Pictures with the Grinch at Otto’s
Free admission for Festival of Trees at Berkshire Museum (5:30 to 8 pm)
Saturday, December 7:
European Holiday Market at the Lower Level of the Beacon Cinema
Berkshire Holiday Bazaar by Thistle ‘n Thorn Floral at Holiday Inn
Clock Tower Artist’s Tinsel and Bling Holiday Art Opening
Free Children Activities Downtown (See below)
Free Kids’ Paint & Sip at St. Stephen’s
Photo Ops with Santa at the Lower Level of the Beacon Cinema
City of Pittsfield’s Park Square Tree Lighting Ceremony: Friday, December 6, 6 pm
The City of Pittsfield’s Park Square Tree Lighting Ceremony will be on Friday, December 6 starting at 6 pm. Join Santa, Mrs. Claus, and the City of Pittsfield’s Recreation Department for this festive holiday tradition. Stick around to meet Santa and Mrs. Claus after the tree is lit.
Hot Chocolate & Pictures with the Grinch at Otto’s: Friday, December 6, 5 to 7 pm
Otto’s Kitchen & Comfort, 95 East Street, will be providing free hot chocolate and photo ops with the Grinch from 5 to 7 pm on Friday, December 6. Stop by before or after The City of Pittsfield’s Park Square Tree Lighting Ceremony which starts at 6 pm.
Wreath Art Auction to benefit the South Community Food Pantry: Friday, December 6, 5 to 7 pm
Pittsfield’s Office of Cultural Development and the Lichtenstein Center for the Arts, 28 Renne Avenue, will host their annual Wreath Art Auction to benefit the South Community Food Pantry on Friday, December 6. Talented local artists have graciously donated their talent, time, and hearts to create beautiful holiday wreaths, centerpieces, and much more that will be sold and auctioned off to benefit the South Community Food Pantry. This year, there will also be a raffle to get a chance to win some amazing gifts. All of the proceeds from this event will benefit the South Community Food Pantry which serves 1200 families a week in Pittsfield.
Grab and go wreaths will be available starting at 5 pm, and the top items will be auctioned off at 6:30 pm following the Tree Lighting Ceremony at Park Square. $10 suggested donation at the door.
Free admission to the “Festival of Trees: Aquatica”: Friday, December 6, 5:30 to 8 pm
The Berkshire Museum, 39 South Street, will offer free admission to the “Festival of Trees: Aquatica” on Friday, December 6 from 5:30 to 8 pm as part of the Festive Frolic. This year’s theme is all about the sea, river, and wetland critters that we know and love. See trees decorated by community members, businesses, and institutions with ties to the community.
European Holiday Market: Saturday, December 7, 12 to 3 pm
Berkshire Holiday Bazaar: Saturday, December 7, 11 am to 5 pm
There will be a Holiday Bazaar hosted by Thistle ‘n Thorn Floral on Saturday, December 7, 11 am to 5 pm, at The Holiday Inn & Suites, 1 West Street, featuring about 50 local vendors selling an array of holiday gifts and special events including a DIY Candle Class with Berkshire Candle; 20-minute sessions with Psychic Medium, Jenna Reid; and caricatures with artist Matt Bernson. Thistle ‘n Thorn Floral will be sponsoring free caricatures for the first two hours of the event. Stay up to date with event details at www.thistlenthornfloral.com.
Photo Ops with Santa: Saturday, December 7, 12 to 3 pm
Free Kids’ Paint & Sip: Saturday, December 7, 12 to 2:30 pm
Downtown Pittsfield, Inc. and St. Stephen’s Episcopal Church will host a Free Kids’ Paint & Sip on Saturday, December 7, 12 to 2:30 pm, in the auditorium at St. Stephen’s Episcopal Church, 67 East Street. There will also be a bonus painting craft on wooden ornaments sponsored by St. Stephen’s.
This free winter-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.
Berkshire Art Center Free Drop-In Art Making: Saturday, December 7, 12 to 3 pm
Join Berkshire Art Center for a Free Drop-In Art Making event at their Brothership Building location, 141 North Street, as part of Downtown Pittsfield’s Festive Frolic Junior on Saturday, December 7, from 12 to 3 pm. A BAC Faculty Artist will be leading a creative snowflake wall hanging project, appropriate for a multigenerational audience — art for all! Attendees can enjoy unguided, drop-in participation. A Faculty Artist will be circulating tables offering encouragement, answering questions, and assisting hands-on.
Create your own Star Ornament: Saturday, December 7, 12 to 3 pm
Peace Train Tees, 2 South Street, will host a free “Create your own star ornament” event on Saturday, December 7 from 12 to 3 pm. Coloring sheets with special markers will be provided, and finished designs will be used to create a completed ornament. The child’s design will be on the front, with the event name and year on the back to look back on for years to come. This event is free and best suited for ages 4 to 12. Parent participation is encouraged, and refreshments will be provided.
Build your own Cotton Ball Snowman: Saturday, December 7, 11:30 am to 2:30 pm
Marie’s North Street Eatery and Gallery, 146 North Street, will host a free “Build your own Cotton Ball Snowman” activity on Saturday, December 7 from 11:30 am to 2:30 pm.
Holiday Card Making Drop-in: Saturday, December 7, 12 to 3 pm
The Berkshire Athenaeum, 1 Wendell Avenue, will host a Holiday Card Making Drop-in on Saturday, December 7 from 12 to 3 pm in the Children’s Library. Kids can make holiday cards for nursing home residents as well as holiday cards for them to take home, while supplies last.
Festive Bookmark Making Drop-in for Adults: Saturday, December 7, 12 to 3 pm
The Berkshire Athenaeum’s Adult Services Department will host a Festive Bookmark Making Drop-in for Adults on Saturday, December 7 from 12 to 3 pm in the Blake Room on the main floor back by the Reference Desk.
Oral History Event: Saturday, December 7, 10 am to 2 pm
The Berkshire Athenaeum, 1 Wendell Avenue, in partnership with the Berkshire County Historical Society (BCHS) will present a free Oral History Event on Saturday, December 7 from 10 am to 2 pm.
In celebration of the 100th anniversary of the publication of Herman Melville’s Billy Budd, the Berkshire Athenaeum and BCHS will collect and record stories of grandparents and grandchildren. Billy Budd was discovered and published by Herman Melville’s granddaughter, Eleanor, who shared a special relationship with her grandfather. Together with partners from the Housatonic Heritage Oral History Center at Berkshire Community College, the Athenaeum and BCHS will create a story scavenger hunt for children and their families, which will include tasty treats and art projects. All participants will receive a copy of their recorded stories.
Pre-registration is not required. This program is funded in part by Mass Humanities, which receives support from the Massachusetts Cultural Council and is an affiliate of the National Endowment for the Humanities.
Free Holiday Pot Decorating Drop-in at The Plant Connector: Saturday, December 7, 12 to 3 pm
The Plant Connector, 46 West Street, will host a free holiday pot decorating drop-in on Saturday, December 7 from 12 to 3 pm and will offer kids’ mini winter-themed terrariums for $12.
Free All Ages Photo Frame Decorating Drop-in: Friday, December 6, 5 to 8 pm; Saturday, December 7, 12 to 3 pm
Witch Slapped, 78 North Street, will host an all-ages free photo frame decorating drop-in event on Friday, December 6, from 5 to 8 pm, and on Saturday, December 7, from 12 to 3 pm.
Balloon Twist for Beginners: Saturday, December 7, 1 to 2 pm
Nene’s Deco, 144 South Street, will host a free “Balloon twist for beginners” class on Saturday, December 7 from 1 to 2 pm.
Tinsel and Bling Holiday Art Opening: Saturday, December 7, 1 to 5 pm
On Saturday, December 7, 1 to 5 pm, the Clock Tower Artists will host a Tinsel and Bling Holiday Art Opening at the Clock Tower Business Center, 75 South Church Street, featuring a festive showcase of unique local art. Discover a dazzling variety of works, including watercolor, oil paintings, abstract art, paint pouring, sculptures, and even one-of-a-kind repurposed clothing. You’ll also find small works of art perfect for gift-giving! Meet the artists, find distinctive holiday treasures, and enjoy light refreshments.
Artists include Karen Carmean, Deborah H Carter, Joan Palano Ciolfi, Randy Foulds, Marion Grant, Nava Grunfeld, Caroline Kelley, Mollie Kellogg, Bruce Laird, Mark Mellinger, Linda Petrocine, Shany Porras, Sally Tiska Rice, Ilene Richard, Audrey Shachnow, Jordan Stone, Sharon Walthew, Stefanie Weber and Carmel Wilson.
Where’s Winston? Scavenger Hunt Kick Off: Saturday, December 7, 10 am
Downtown Pittsfield, Inc.’s Where’s Winston? Scavenger Hunt will kick off on Saturday, December 7, at 10 am. To play, go to the Children’s Library at the Berkshire Athenaeum to pick up your Game Card. Then go to the locations on the Game Card, find the Winston posters, and write down the words. Bring your Game Card back to the Children’s Library to claim your prizes. The Where’s Winston? Scavenger Hunt will run through Friday, January 3, 2025 while supplies last. Click here to see full game details.