Kids Events in Winchester, MA

Ready to give your child some independent playtime in a safe, nurturing space? Play School Drop Off at The Village Playspace offers a once-a-week program for little ones ready to explore, learn, and play on their own terms with trained staff nearby. It's a wonderful way to build confidence and independence while you enjoy some well-deserved personal time.

via Google Events

Ready to celebrate live music and community spirit right on the porches of Somerville? "PorchFest" on Friday, May 8,Saturday, May 9, 2026, transforms neighborhoods into open-air concert venues where families can enjoy free or low-cost performances. This beloved Somerville tradition brings neighbors together and offers kids a fun, walkable way to discover local musicians and artists.

via PorchFest Somerville

Ready to experience Somerville's most vibrant musical festival as a family? PorchFest Somerville on Saturday, May 9, 2026 transforms neighborhood porches into live performance stages across the entire city. Families can stroll from porch to porch discovering local musicians and artists,rain or shine,making it a unique, FREE way to celebrate community culture right in your own backyard.

via PorchFest Somerville

Get ready for jaw-dropping acrobatics and non-stop laughter at Cirque Us Extravaganza, coming to Wheelock Family Theatre in Winchester, MA. Featuring jugglers, clowns, contortionists, aerialists, and acrobats from world-renowned circus companies, this high-flying performance will leave your whole family mesmerized by incredible feats of skill and artistry.

via Wheelock Family Theatre

Discover an enchanting way to create art this summer at the Cyanotype Family Fun Workshop at Brookline Arts Center, 86 Monmouth St, Brookline, MA. Families will explore the magic of sun printing,an exciting technique that's been used for over 150 years,by foraging for natural materials and creating one-of-a-kind prints. This hands-on outdoor workshop on Friday, June 12, 2026, is perfect for creative kids ages 6 and up who love experimenting with nature and light.

via Google Events

Feeling like date night is impossible to arrange? Date Night at The Village Playspace (64 Salem St, Medford, MA) solves the sitter stress by providing trusted, quality childcare while you and your partner enjoy time together. Your child will have a blast in a safe, fun environment, so you can actually relax and reconnect.

via Google Events

Want to make theater night extra special? The Red Carpet Meet & Greet at Wheelock Family Theatre in Winchester is a FREE opportunity for young theater fans to get autographs and take pictures with the cast right after every 2:00 pm matinee on Monday, October 5, 2026. It's the perfect way to extend the magic and create lasting memories with your family.

via Wheelock Family Theatre

Give your budding dancers a backstage experience at the FREE Pre-Show Choreography Workshop at Wheelock Family Theatre in Winchester on Sunday, October 11, 2026. Before evening performances, cast members lead this hands-on dance workshop from 6:30 pm to 7:15 pm, giving families an insider's peek at the choreography they'll see on stage.

via Wheelock Family Theatre