Pittsfield Announces 3rd Annual Winter Festival at Clapp Park
PITTSFIELD, Mass. — Pittsfield's Department of Community Development Recreation Program has announced its third annual Winter Festival for Monday, Feb. 16, from 10 a.m. to 1 p.m. at Clapp Park.
As a kickoff to winter break for local Pittsfield schools, this year's festival will include a variety of outdoor activities for children and their families including:
Cardboard Sled Design Contest & Races
Prior to the day of Winter Festival, all children and families are asked to construct their own cardboard sled at home using glue, tape, paint, and decorations. No plastic or purchased sleds are allowed. Awards will be given for Best Use of Materials, Most Creative Sled and Largest Sled Design.
In preparation for the contest, RSI Signs is offering a free Cardboard Sled Building Workshop on Saturday, Feb. 7, from 1-3 p.m. at their sign shop located at 20 Yorkshire Ave, Pittsfield.
Basic supplies, including cardboard, will be provided and kids of all ages are welcome to attend. Parents or guardians must be present at the workshop to assist their child(ren) with building. Families must also take their sleds home after the workshop and bring them to Clapp Park on Monday, February 16, to participate in the contest at Winter Festival. Interested families can sign up for the workshop by emailing orders@rsi-signs.com.
On the day of Winter Festival, all participants for the Cardboard Sled Design Contest must register at the Pittsfield Parks & Recreation table in the back parking lot of Clapp Park by 10:30 a.m. Awards will be announced at 11 a.m. and contestants will then take part in cardboard sled races at the sledding hill.
Group Led Activities
- Snowshoeing with Mass Audubon
- Winter Basketball Foul Shooting Contest with 18 Degrees' Youth Development Team
- Winter-themed Carnival Games with 18 Degrees' Family Resource Center
Snow Building Sculpture Contest
For beginners to professional artists, create a snow sculpture of any form to be entered into the contest. Weather permitting and with enough snow, sculptors are asked to bring their own snow carving and building tools. Artists can begin their work at the start of the festival and judging will take place by the end of the day. This contest is open to participants of all ages, including children.
Touch-A-Truck
Families are invited to get up close with big vehicles that keep the city moving during the winter season from the Department of Public Works, Fire Department, Parks Department and the Pittsfield Municipal Airport. Pending no city emergencies, vehicles, trucks and other equipment will be stationed in the back parking lot of the park for families to interact with alongside staff who operate them.
Face Painting
Face painting by RSI Signs will be available during this year's Winter Festival. This activity will feature festive, winter-inspired designs for children of all ages.
All activities at the Winter Festival are free to the community. A small campfire, managed by Park Maintenance staff, will be available to stay warm. In addition to the lineup of activities, Gateway Fiber will be giving away free winter gloves to the first 150 attendees at the event. Berkshire Kettle Creations & Lemonade will also be providing free samples of kettle corn for children at the event.
The Recreation Program's Winter Festival event is taking place during the City of Pittsfield's 15th annual 10x10 Upstreet Arts Festival hosted by the Cultural Development Office from February 12-22, 2026. To check out more events scheduled during the 10x10 Festival visit: www.lovepittsfield.com/10x10/
