Family events in Winchendon, MA

A warm, child-centered morning designed for infants, toddlers, and their caregivers features engaging stories, lively songs, and developmentally supportive play. It offers an easy way to meet other families while little ones explore at their own pace. This program is free, light refreshments are available for children and adults, and walk-ins are welcome with no registration needed.

A casual teen drop-in at The HUB features free bowling, ice cream, and space to relax with friends. The atmosphere is laid back with games to enjoy and no admission cost, creating an easy place to unwind. Sponsored by The United Way of North Central MA.

The cruise night returns with a new name honoring beloved member Bruno Starzynski. Expect a classic car showcase that depends on the weather, a visiting food truck, and a 50/50 raffle. Live bands perform in the Pavilion Hall regardless of conditions. Admission is free and the event is open to the public.

The NEECA Triathlon brings a team-focused challenge with three legs that include biking, running or jogging, and horseback riding. Each team designates one participant for each segment, and recognition is given for the fastest combined team time as well as top individual times in each category. With a welcoming atmosphere for families and friends, it blends friendly competition with plenty of fun.

A Mopar-focused car show at Salvadore Chrysler Dodge Jeep RAM in Gardner, Massachusetts brings together classic vehicle owners, passionate fans, and spectators to celebrate the cars, the community, and the shared Mopar spirit. Explore a lineup of classic Mopars, enjoy food available for purchase, test your knowledge with trivia, and take part in prize opportunities. The gathering also highlights two milestones, recognizing Salvadore’s 35 years in business and the Mighty Mopar Group’s 42nd year as a club. Admission is free.

HHF’s annual Apple Festival features pick-your-own apples, local vendors, live music, and seasonal food and drinks. Food is provided by The Finicky Fork, and the music lineup includes Ethan & Ashley, Blue Collar Ramblers, and The Blue Hour Society. Vendor applications are open, and questions can be sent to Michelle at mdicastro15@gmail.com. Additional details will be shared as they become available.

Celebrate the close of the season at the Community Canvas End of Summer Festival. Explore hands-on maker tables, enjoy live music from Shaely O'Dou, sample bites from food trucks, and cap it off with a movie. Admission is free, with support from Mass Cultural Council, Athol Credit Union, Athol Trading Post, POLUS CENTER, Athol Area YMCA, and Lickity Splitz.