Wellesley Family-Friendly Fall Activities 2025

Experience the quintessential fall at Belkin Family Lookout Farm. Wander through their historic orchards, picking fresh apples and Asian pears. Kids and adults alike can enjoy the expansive play areas, including a challenging corn maze and tractor-themed fun. Savor farm-fresh...

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...

Youngsters aged 2-5 are invited to a special Halloween Storytime and Parade. This isn't your typical storytime; come dressed in costume to enjoy spooky tales, create a Halloween craft, and march in a festive parade around the library.

Celebrate the season with a delightful fall festival at Gore Place. Families can get creative stuffing and decorating scarecrows, painting pumpkins, and enjoying a classic hayride. It's a perfect way to embrace autumn fun on the historic farm.

Join the Metropolitan Waterworks Museum for a ghoulishly good time at their Tricks and Treats event. Families can collect candy, create spooky crafts like balloon rocket bats and monster microbe puppets, and march in a costume parade. Special access to...

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,...

Experience the magic of fall at Wilson Farm's annual Pumpkin Festival. Wander through a charming Pumpkin Village, complete with themed houses and a Wild West town, perfect for capturing festive photos. Indulge in hot apple cider donuts and caramel apples...

Get ready for a spooktacular time at the second annual BARKTOBER: Halloween Pup Party & Parade! Dogs can strut their stuff in their best costumes for a chance to win great prizes. The event features a fun pup social, a...

Get ready for a spooktacular time at Prudential Center's 31st annual PruBoo event! This family-friendly Halloween celebration features trick-or-treating at over 30 participating stores and restaurants. Kids can enjoy face painting, Halloween crafts, captivating magic shows, and a lively musical...

Get ready for a spooktacular afternoon at the Halloween Block Party and Pet Spooktacular! This signature event features a beloved pet costume contest, live music, delicious food from local vendors, and fun activities for everyone. It's the perfect way to...

Join the City of Boston for the annual Fall-o-Ween Children's Festival at the Boston Common Frog Pond. This free event encourages families to wear costumes and enjoy a spooky good time with a haunted zombie maze, pumpkin slide, trackless train...

Immerse yourself in Medford's largest arts festival at the Condon Shell. This vibrant event features live music across multiple genres, a bustling marketplace of local artisan crafts, and engaging activities for all ages. Discover unique handmade treasures, savor delicious food...

Experience a thrilling Halloween celebration at the Museum of Science with Spooky Science Sunday. This all-ages event features a costume dance party with DJ Ooch, engaging hands-on activities, and captivating live science presentations. Discover the wonders of chemistry, meet live...

Fairmount Fruit Farm in Franklin, MA, hosts a variety of family-friendly events throughout the year. Visitors can enjoy seasonal hayrides, unique 'Sl'hay' rides, and interactive experiences like goat yoga and coffee with goat cuddles. They also feature 'Touch a Truck...

High Street Place transforms into a festive autumn destination for Fall Fest 2025. This vibrant downtown Boston food hall offers a cozy escape with seasonal flavors, craft beverages, and live music. Explore 20 unique eateries, enjoy DJ sets, and participate...

Join the Boston Public Market for a delightful Community Pumpkin Stroll and Family Halloween Fun event. This festive day includes a scavenger hunt for colorful pumpkins along The Greenway, leading to the Market where giant pumpkins await. Families can enjoy...

Fall into frightful fun at Boston Children's Museum this October! Explore the 'Pumpkin Patch of Play' with themed activities, talking Jack-o'-Lanterns, and a Monster Mash Jam. Don't miss the 6th annual 'Halloween Spooktacular' after-hours event, featuring trick-or-treating, games like Zombie...

Bring your furry friends to The Anchor for a spooktacular Yappy Hour! This Halloween-themed event features a 'Howl-o-Ween Pup Pageant' costume contest with prizes for the best-dressed dogs. Enjoy live music, complimentary pup cups, free swag, and delicious treats in...

Discover the charm of Honey Pot Hill Orchards, a family-run farm since 1926. Engage in classic fall activities like apple picking, navigating the thrilling Monster Maze, and enjoying scenic hayrides. Savor fresh donuts and explore the farm store for seasonal...

Bring the little ones for a spooktacular Halloween brunch at Pazza on Porter! Kids can showcase their costumes while enjoying sweet treats and a family-friendly atmosphere. Adults can savor seasonal drink specials alongside a full brunch menu available a la...

Join the Council on Aging for a spirited Halloween celebration at the Edward G. Connolly Center. Attendees can enjoy a delicious catered lunch, dance to music by DJ Tommy Sheehan, and show off their festive attire in a costume contest...

Join the 16th Annual Trick or Treat in Malden Square for a festive Halloween celebration. Kids 12 and under can follow a special treasure map to collect candy and treats from participating locations. Meet costume characters and members of the...

Fort Independence hosts its beloved Children's Magical Halloween Castle event, offering a delightful and spooky experience for families. Attendees can immerse themselves in the historic fort, which is transformed with colorful decorations. The event features captivating spooky storytelling sessions and...

Get ready for a spooktacular time at Stone Zoo's Boo at the Zoo! This family-friendly Halloween celebration invites visitors to wander through animal habitats, collect treats on a special trail, and enjoy engaging keeper chats. Little ones will delight in...

Join the Malden Chamber of Commerce for their 21st Annual Trick or Treat event! This festive gathering in City Hall Plaza is perfect for families. Children aged 12 and under can grab a special Treasure Map to navigate the area...

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...

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...

Get ready for a 'Monster Mash' at Weymouth's Halloween Trunk-or-Treat! This festive event combines trick-or-treating from decorated car trunks and tents with live music from The Wolfpack. Families can enjoy spooky guests, delicious food truck offerings, and a fun-filled afternoon...

Adams Farm invites visitors to embrace the autumn season with a classic pumpkin patch experience and exciting hayrides. Explore their expansive corn mazes, including a mega hay maze and a special kids' version, perfect for family fun. Get up close...

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...

Wojcik's Farm offers classic fall fun with a sprawling five-acre corn maze and scenic tractor-driven wagon rides. Challenge yourself to find three hidden checkpoints within the maze for a chance to win cash prizes. Relax and enjoy the picturesque countryside...

Embark on a magical Halloween adventure at Krochmal Farms with their unique trick-or-treating hayride. Families and friends can climb aboard a cozy hayride, pulled by gentle draft horses, as they journey through the farm's enchanting landscape. Along the way, costumed...

Experience a quintessential New England fall at Krochmal Farms' annual Pumpkin Festival. Just a short drive from Boston, this 4th-generation family farm offers a delightful escape with a vast pumpkin patch, scenic horse-drawn hayrides, an exciting corn maze, and opportunities...

Get ready for a spellbinding time at the Hocus Pocus Halloween Skate! Join the Sanderson Sisters for an afternoon of spooky fun and roller skating. Dress in your best costume and enjoy a magical skating experience. It's a perfect way...

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...

Join the Woonsocket Harris Public Library for a spooktacular Halloween celebration! This family-friendly event features face painting, exciting games, creative crafts, and a chance to win prizes. Kids are encouraged to come dressed in their favorite costumes for a festive...

Discover a delightful Halloween day at Good Pickin' Farm, designed for family fun without the scares. Enjoy a not-so-spooky hayride, a treat scavenger hunt, and a petting zoo featuring costumed animals. All activities, including crafts and a bonfire, are included...

Experience the West End Creamery's Fall Festival & Corn Maze, a 28-acre celebration of autumn fun. Get lost in a 5-acre corn maze honoring American history, enjoy included attractions like pedal carts and a cow train, and take a scenic...

Get ready for the Annual Monster Bash, a FREE family event hosted by the Kiwanis Club of Greater Lowell! This exciting Halloween celebration features a thrilling haunted house, engaging games, and activities for all ages. Join the fun as part...

Join the North Shore Children's Museum for their third annual Halloween Costume Party! This family-friendly event features face painting, festive crafts, games, and unique Halloween touch boxes. Enjoy fresh popcorn while exploring the museum's engaging exhibits. Tickets must be purchased...