Family-Friendly Fall Activities Near Winchester 2026

Boston Children's Museum invites families to a 'Pumpkin Patch of Play' this October, featuring a variety of Halloween-themed activities. The highlight is the 7th annual Halloween Spooktacular, an after-hours event with trick-or-treating, games, and character meet-and-greets. Throughout the month, enjoy...

Experience Boston's beloved FREE Halloween event at Fort Independence in 2026. This family-friendly celebration transforms the historic fort into a magical Halloween Castle, perfect for kids in costume. Enjoy spooky storytelling, complimentary face painting, and explore eight uniquely themed rooms...

The Fall-o-Ween Children's Festival transforms Boston Common Frog Pond with a Haunted Zombie Maze, pumpkin slides, live music, magic shows, and arts and crafts.

Krochmal Farms' annual Pumpkin Festival includes a pumpkin patch, hayrides through autumn foliage, and a corn maze. Visitors can also go on pony rides, interact with farm animals, and purchase food. A Safe Trick or Treat hayride is offered.

Gore Place hosts a family-friendly Halloween event with workshops and historical exploration. Activities include needle felting, Japanese mending, and a puppet class for preschoolers. Visitors can tour the 1806 Mansion and see sheep shearing.

Stone Zoo's Jack-O'-Lantern Nights offers a fall celebration. Options include private tent rental, glow batons, and themed decorations. Thousands of glowing pumpkins are on display.

A Halloween scavenger hunt in Union Square tests neighborhood knowledge. Participants have three hours to complete the hunt, starting and finishing at Aeronaut's Somerville taproom. Completion earns a commemorative glass and bragging rights. The event is followed by a Halloween...

Aeronaut Brewing Company hosts its annual pumpkin carving event. Attendees receive a pumpkin from Wilson Farm and carving tools to create Halloween decorations while enjoying fall beers. Ticketed sessions are available.

Villari's Martial Arts hosts its 2nd Annual Fall Festival at Lincoln Park. This free event includes martial arts classes, fun fights, and seasonal treats for families.

Arsenal Yards hosts its annual Fall Falladays Festival, offering free seasonal entertainment. Attendees can enjoy carnival games, live music from a DJ and a band, and an aerial performance. Complimentary fall treats, kid's crafts, and fire pits are available. Advance...

Boston Landing's Fall Festival is a free, family-friendly, Western-themed event. It features live music from Lexi James & Wildheart, a live DJ, and line dancing lessons. Children's activities include pony rides, reptile encounters, craft stations, and pumpkin decorating. Food options...

The BU Global Programs Office holds a mini pumpkin decorating event. Participants paint a mini pumpkin to take home, with light snacks and refreshments provided.

Lansdowne Pub offers weekly pumpkin carving sessions every Wednesday evening in October, providing a pumpkin, carving kit, and paint. Fall-themed cocktails are available.

Boston's city-wide festival celebrates autumn with food, music, and local culture. Visitors can view colorful leaves, taste seasonal treats, and enjoy live entertainment.

Prudential Center's 32nd annual PruBoo event on Sunday, October 25th, is a family-friendly Halloween celebration. Children can trick-or-treat at participating stores and restaurants. Activities include face painting, Halloween crafts, magic shows, and a musical performance.

Families can attend a free fall-themed event at the Boston Women's Market, featuring pumpkin painting and face painting. Local women-owned businesses will be present. Lawn games, a reading corner, and a photo booth are also included.

Children aged 5-11 can enroll in the Stage Sprouts Fall 2026 program for weekly acting classes every Thursday from September 24th to November 12th, concluding with a performance in Fiske Hall.

The Food Project's annual fall festival includes live music, dancing, food, and a beer and cider garden. Families can pick pumpkins and bid in a silent auction to support The Food Project.

Malden Square's 16th Annual Trick or Treat event offers candy collection for children 12 and under via a treasure map. Attendees can also meet costume characters, police, and fire department members, and participate in crafts.

Prudential Center's 31st annual PruBoo event offers family-friendly trick-or-treating, face painting, crafts, and a magic show.

Lace up for the Revere Beach Partnership Pumpkin Dash, a lively 5K road race and kid's fun run set against the scenic backdrop of Revere Beach. After the race, enjoy a Fall Festival featuring live music, cookie decorating, and a...

Stone Zoo's Boo at the Zoo is a family-friendly Halloween event. Visitors can tour animal habitats, collect treats, attend keeper chats, and enjoy storytimes. Animals will receive Halloween-themed enrichment. A VR experience, 'Jinxed,' is also offered.

The Halloween Block Party and Pet Spooktacular features a pet costume contest, live music, and food from local vendors. Activities are available for all.

The Museum of Science's Spooky Science Sunday is an all-ages event with a costume dance party, hands-on activities, and science presentations on chemistry, animals, electricity, and robotics.

Celebrate the season at Drumlin Farm Wildlife Sanctuary's Fall-o'ween on the Farm! This popular event offers a festive hayride through autumn foliage, a chance to explore the Creepy Critter Mansion, and a fun-filled Hay Play area. Visitors can enjoy crafts,...

Wilson Farm's annual Pumpkin Festival includes a Pumpkin Village, hot apple cider donuts, and caramel apples. A raffle supports Make-A-Wish, and a Haunted Gingerbread House Workshop is offered.

Boston Public Market offers a Community Pumpkin Stroll along The Greenway, leading to giant pumpkins at the Market. Families can participate in Halloween crafts and cookie decorating.

This annual Halloween Pup Party & Parade invites furry friends to showcase their costumes. Dogs can participate in a parade and contest with prizes for best individual and group costumes. Attendees can also enjoy vendor booths offering treats and activities,...

Medford's largest arts festival takes place at the Condon Shell, featuring live music, artisan crafts, and activities for all ages. Food vendors and face painting are available.

Gather at the Waterworks Museum for a ghoulishly good time with Tricks and Treats. Kids can collect candy, create crafts like balloon rocket bats and monster microbe puppets, and make their own musical instruments for a costume parade. Enjoy Halloween-themed...

North Shore Children's Museum's third annual Halloween Costume Party, for families, includes face painting, crafts, games, touch boxes, and popcorn. Advance ticket purchase is required; walk-ins are not permitted.

The Council on Aging will hold a Halloween Party at the Edward G. Connolly Center. Attendees can enjoy a catered lunch, music by DJ Tommy Sheehan, and a costume contest.

This Halloween-themed Yappy Hour event welcomes four-legged friends for a special Pup Pageant costume contest. Hosted at The Anchor, the event offers pup cups for dogs and prizes for the best costumes. Attendees can enjoy the venue's pet-friendly courtyard, live...

Pazza on Porter hosts a free Kid's Halloween Brunch featuring costumes, candy, and family fun. Children can enjoy a dedicated photo corner and receive candy, while the full brunch menu is available a la carte, including kid-specific options. Adults can...

Newton's Halloween Window Painting event invites students in grades 3-8 to transform storefront windows into festive Halloween canvases. Participants can unleash their creativity with spooky designs in one of seven participating villages. This cherished tradition offers a safe and engaging...