Things to Do for Kids in Boston in October 2026
Incredible Naumkeag Pumpkin Show
Stockbridge
October 1- 31, 2026
Cauldrons, cobwebs, fairy houses, volcanoes, and—the star attractions—thousands of jack-o’-lanterns, mums, pumpkins, and gourds transform Naumkeag into an autumnal haven. Website
Topsfield Fair
Topsfield
Friday, October 2-October 12, 2026
The Topsfield Fair is the quintessential country fair - traditional agricultural exhibits, big entertainment, rides, games, shopping, and great food. Website
King Richard's Faire
Carver
Weekends through October 25, 2026
A visit to King Richard’s Faire, New England’s largest and longest-running Renaissance festival that is tucked away on 80 acres of enchanted forest, offers a full day of live, interactive entertainment. Website
Tales and Tombstones Tour of Salem
Salem
Weekends through October 29, 2026
See the spookier side of Salem in these one-hour nighttime trolley tours past graveyards, haunted houses, underground passageways, and more. Website
Phantoms by Firelight at Old Sturbridge Village
Sturbridge
Weekends, October 3-October 25, 2026
This beloved living history museum comes to life after dark and puts a Colonial-times spin on Halloween with a haunted outdoor experience. Explore the wooded grounds and village green after hours to discover bats, bonfires, ghosts, hidden candy, and even a headless horseman. Website
Jack-O-Lantern Spectacular
Providence, RI
October 2-31, 2026
Celebrate the Halloween season with a visit to Roger Williams Zoo's Jack-O-Lantern Spectacular. Stroll through a path that features thousands of intricately carved pumpkins. Website
Return of the Pumpkin People
Jackson, NH — FREE
October 1 - 31, 2026
It's the Return of the Pumpkin People! Take a self-guided tour of a variety of Pumpkin People at more than 60 different displays. See Pumpkin People doing all kinds of things from flying across yards to deep-sea diving. Website
Sensory-Friendly Boo in the Barnyard
Southborough
Saturdays, October 3, 17, & 31, 2026
Join a festive scavenger hunt, create a seasonal craft, and enjoy a sweet treat. After visiting the Barnyard, hike the woodland trails surrounding Weir River Farm to explore and experience all the beauty of Weir River Farm in the fall! Website
Berkshire Harvest Festival
Berkshire Botanical Garden, Stockbridge
Saturday, October 10-11, 2026
Scarecrows will be displayed throughout the Garden during the Harvest Festival. Attendees will vote on their favorites. Read More
Mad Love Music Festival
Hingham
Sunday, October 11, 2026
This outdoor festival features local musicians, food, drink, and activities for the whole family. Website
Head of the Charles Regatta
Boston — FREE
Friday, October 16 - 18, 2026
Since 1965, rowers have come from far and near to the banks of the Charles River to take part in the world's largest regatta. Website
Jack-O'-Lantern Nights at Stone Zoo
Stoneham
Weekends, October 1- 31, 2026
Stone Zoo will transform into a glowing autumn wonderland after dark, with hundreds of illuminated pumpkins, larger-than-life sculptures, and plenty of family-friendly Halloween fun. Website
Annual AppleFest at Wachusett Mountain
Princeton
Saturday & Sundays, October 17 - 25, 2026
Wachusett Mountain’s 42nd annual AppleFest is the ticket to both, featuring every apple-flavored treat from candy to cocktails, and one of the most unique bird’s-eye views of Fall foliage in Massachusetts. Website
Boston Book Festival: Copley Square
Boston — FREE
Saturday, October 17, 2026
Boston Book Festival hosts author presentations, panels, and hands-on demonstrations at outdoor venues throughout the Copley Square area, from Trinity Church to the Boston Public Library. A street fair in the square features exhibitors and live music throughout the day. Website
Halloween On The Hill
Beverly
Multiple Dates in October 2026
An enchanting woodland hides an eerie graveyard, haunted pirate ship, stylish scarecrows, and thousands of hand-carved glowing jack-o’-lanterns. Website
Halloween Glow in the Park at TreeTop Adventures
Canton
Saturday, October 31, 2026
Wear a costume and enjoy colored lights and music while climbing through the tree tops on this zip-line obstacle course. Website