Family-Friendly Fall Activities Near Randolph 2026

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...

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...

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.

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.

The Old Colony YMCA Easton Branch hosts its annual Trunk or Treat event, offering a safe environment for families to trick-or-treat from decorated car trunks.

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.

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.

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

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.

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.

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.

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...

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...

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.

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.

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...

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...

Weymouth's Halloween Trunk-or-Treat combines trick-or-treating from decorated car trunks and tents with live music from The Wolfpack. The event includes spooky guests and food trucks.

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.

Belkin Family Lookout Farm Fall Festival allows apple and Asian pear picking. The farm features play areas, a corn maze, tractor-themed fun, and farm-fresh food and beverages.

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

Get lost in the twists and turns of the impressive corn maze at Flint Farm. This seasonal attraction offers a fun challenge for all ages. Complement your maze adventure with a delightful hayride, providing a scenic tour of the farm's...

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,...

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.

Belkin Family Lookout Farm provides seasonal fruit picking, a corn maze, and play areas. A taproom serves farm-to-table BBQ and house-made ciders and beers.

Celebrate Halloween at Weir River Farm by dressing up and meeting the beloved barnyard animals. Families can enjoy a fun scavenger hunt, create a seasonal craft, and savor a sweet treat. Afterward, explore the farm's woodland trails to soak in...

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...

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.

The Hocus Pocus Halloween Skate is a roller skating event featuring Sanderson Sisters characters. Costumes are encouraged for the skating activity.

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.

Sauchuk's Corn Maze & Pumpkin Patch offers a quintessential fall experience with a massive corn maze and a bountiful pumpkin patch. Families can enjoy a variety of activities, including hayrides, games, and the chance to pick their own pumpkins. It's...

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...

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...

Fashion illustrator Holly Nichols leads a Halloween-themed coloring event. Participants can bring their own supplies or purchase them on-site. Costumes are optional.

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...

This delightfully entertaining haunted house is perfect for preschool and elementary-aged children. Guests will encounter friendly ghosts, witches, and pirates, and can enjoy a Halloween party with crafts, games, and storytelling afterward. It's an annual tradition for families seeking a...