Best Events for Kids in Boston in October 2025

Best Things To Do in Boston October 2025 with Kids

Incredible Naumkeag Pumpkin Show
Stockbridge
October 1- 31, 2025
Naumkeag's famous gardens in the Berkshires are adorned with 1,500 jack-o-lanterns, hundreds of mums, and exciting gourds. There will be hot cider and treats. Visit the website here.

Return of the Pumpkin People
Jackson, NH — FREE
October 1 - 31, 2025
It's the 41st annual Return of the Pumpkin People! Take a self-guided tour of a variety of Pumpkin People at more than 50 different displays. See Pumpkin People doing all kinds of things from flying across yards to deep-sea diving. Visit the website here.

Topsfield Fair
Topsfield
Friday, October 3- October 13, 2025
The Topsfield Fair is the quintessential country fair - traditional agricultural exhibits, big entertainment, rides, games, shopping, and great food. Visit the website here.

King Richard's Faire
Carver
Weekends through October 19, 2025
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. Visit the website here.

Tales and Tombstones Tour of Salem
Salem
Weekends through October 30, 2025
See the spookier side of Salem in these one-hour nighttime trolley tours past graveyards, haunted houses, underground passageways, and more. Visit the website here.

Phantoms by Firelight at Old Sturbridge Village
Sturbridge
Weekends, October 10-October 26, 2025
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. Visit the website here.

Jack-O-Lantern Spectacular
Providence, RI
Daily through Sunday, November 2, 2025
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. Visit the website here.

Sensory-Friendly Boo in the Barnyard
Southborough
Saturdays, October 11 &. 18, 2025
Take part in a festive scavenger hunt, create a seasonal craft, and enjoy a sweet treat. After your visit to the Barnyard, hike the woodland trails surrounding Weir River Farm to explore and experience all the beauty of Weir River Farm in the fall! Visit the website here.

Berkshire Harvest Festival
Stockbridge
Saturday, October 11-12, 2025
Enjoy live music and entertainment, fresh local and artisan food and refreshments, a plant sale and farmer's market, pony and hay rides, haunted house, hay jump, regional vendors, as well as some surprises still in the works. Visit the website here.

Mad Love Music Festival
Hingham
Sunday, October 12, 2025
This outdoor festival features local musicians, food, drink, and activities for the whole family. Visit the website here.

Head of the Charles Regatta
Boston — FREE
Friday, October 17 - 19, 2025
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. Visit the website here.

Stone Zoo’s Boo at the Zoo
Stoneham
Saturday, October 18 - 19, 2025
Children are invited to trick-or-treat among the animals at Stone Zoo. Thrills, chills, and animals lurk around every corner on the trick-or-treat trail, while other haunted happenings include mystery animal encounters, costume contests and a scavenger hunt with prizes! Visit the website here.

Annual AppleFest at Wachusett Mountain
Princeton
Saturday & Sundays, October 18 - 26, 2025
This all festival celebration includes over 100 craft exhibitors, a farmers' market, kids entertainment, and peak fall foliage viewing from the SkyRide. Visit the website here.

Boston Book Festival: Copley Square
Boston — FREE
Saturday, October 25, 2025
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. Visit the website here.

Halloween On The Hill
Beverly
Multiple Dates in October 2025
Long Hill transforms into a celebration of autumn and the Halloween season. Follow their seasonal-themed trail that will feature over 1,500 hand-carved jack-o'-lanterns, hundreds of mums and pumpkins, elaborate Halloween sets, light displays, music, and more. Visit the website here.

Zoo Howl at Franklin Park Zoo
Dorchester
Saturday, October 25 - 26, 2025
Thrills, chills, and animals await at Franklin Park Zoo’s annual Zoo Howl! During this popular Halloween event, children are invited to trick-or-treat among the animals at the Zoo. Visit the website here.

Halloween Glow in the Park at TreeTop Adventures
Canton
Saturday, October 25, 2025
Wear a costume and enjoy colored lights and music while climbing through the tree tops on this zip-line obstacle course. Visit the website here.