Family events in Southbridge, MA

Celebrating its tenth year, the Harvest Craft Fair at Brookfield Orchards brings together crafters. Applications from crafters are currently being accepted and can be requested by calling 508-867-6858 or emailing BROOKFIELDO@AOL.COM. A poster announcing the participating crafters will be shared soon.

That’s Entertainment hosts a free Pokémon Trading Card Game league for players of all ages. Bring a deck to play, or learn the game with help on site. Children 12 and under must have a parent or guardian present. Attendance is rewarded with prize packs. Please check for any schedule updates before heading out. Questions about the game can be sent to Pokémon Professor Jeff at obijeff@outlook.com.

UNO Pizzeria & Grill hosts a family-friendly Kids’ Night built around food and simple fun. When an adult entrée is ordered, a kids meal is included at no extra cost. Children can stay busy with coloring pages and hands-on play using bright, colorful dough balls, and the menu features kid-approved choices. It creates an easy outing where little ones are entertained and adults can relax over a meal.

Youth ages 10 to 17 can help shape the library by serving on the Youth Advisory Board. The group meets regularly to enhance the library experience, plan programs and events, suggest additions to the library collection, and contribute in other ways. It is an opportunity to take part in shaping what happens at the library.

A cruise night style car show at UNO’s welcomes classics, customs, daily drivers, and everything in between. Best of Show prizes are offered, and each car participant receives a 25% off coupon to use at the restaurant. Families can look forward to games for the kids and a family friendly setting for car enthusiasts of all ages.

A recurring meetup for Central Massachusetts families focuses on babywearing and playtime at The Little Barn Playhouse in Sturbridge. It offers a welcoming space for caregivers to share tips about carriers, get guidance on fit, and enjoy a snack while children explore. Participants can bring a personal carrier for support or try options from the Orange Lending Library. Attendance is free, with a separate playspace fee of $10 for one child and $5 for each additional child over age one. Borrowing from the lending library involves a $10 donation per carrier for a month. For everyone’s well-being, please stay home if you or your child are ill, have a fever, are vomiting, or show symptoms that could put a newborn at risk.

Designed for babies, toddlers, and preschoolers with their caregivers, this casual half hour features popular children's songs. Registration is not required.

REC Farmers Market at University Park features fresh, locally grown produce and baked goods, along with opportunities to connect with community organizations. Vendors include Harper's Farm & Garden, Fay Mountain Farm, Coolidge Hill Farm, Circling Carrots Farm, Wooden Bakery, and others. Payment options include cash and cards, SNAP with HIP benefits, and Senior and WIC Farmers Market Coupons. Parking is available in the Clark University lot on Gates Street.

An engaging children-only market that turns entrepreneurship into a learn-by-doing adventure. Kids choose what to sell, build a booth, talk with customers, and manage money, gaining confidence in innovation and leadership while competing in a lively setting. The program began in Utah, sold out for five consecutive years, and has supported nearly 10,000 young participants, with a stated goal of reaching every state by the end of 2025. Families often highlight how the combination of learning and earning makes the experience both distinctive and fun. More and more markets also welcome returning youth vendors who are ready to deepen their skills and grow their small businesses.

Family Weekend comes to Fitton Field alongside an Education Appreciation Day recognizing the contributions of the education community. Educators can receive free tickets with options for additional discounts.

Polar Park hosts a spirited celebration of Rutland with the WooSox, bringing residents together to show hometown pride and enjoy a day at the ballpark. Every ticket purchased through the special offer directs $5 to a nonprofit organization in Rutland, turning a game outing into meaningful community support. Groups of 15 or more can look into added experiences that put them closer to the action, and local businesses have opportunities to back the town takeover. It is all about baseball, community, and giving back.