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20 Best Things To Do in Boston October 2023 with Kids

Halloween fun is coming to town with the best things to do in Boston with kids this October! Photo courtesy of the Roger Williams Park Zoo and Carousel Village
Halloween fun is coming to town with the best things to do in Boston with kids this October! Photo courtesy of the Roger Williams Park Zoo and Carousel Village
9/29/23 - By N Ferreira

Fall is in full swing, and the best things to do in Boston this October include outdoor festivities and autumn fun! Meet your favorite author at the Boston Book Festival, or whirl and twirl on the rides at America's oldest county fair. And, of course, here come the Halloween celebrations! Walk in famous gardens lit up by 1,500 jack o' lanterns, or trick-or-treat among the animals at the Franklin Park Zoo or Stone Zoo. 

Along with all these special events, fall in New England brings tons of seasonal fun so make sure to check our full Fall Fun Guide. If you're looking for learning activities and enrichment, check out our Classes and Activities Guide for Boston kids for the best classes in the area.

Read on to find out what Boston in October has in store for your family!

 

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Ye olde family fun is easy to find this October! Photo courtesy of King Richard's Faire
Ye olde family fun is easy to find this October! Photo courtesy of King Richard's Faire

Best Things To Do in Boston October 2023 with Kids

Incredible Naumkeag Pumpkin Show

Stockbridge—Friday, September 30 - October 29, 2023
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. READ MORE

Topsfield Fair

Topsfield—Friday, September 29, 2022 - October 9, 2023
The Topsfield Fair is the quintessential country fair - traditional agricultural exhibits, big entertainment, rides, games, shopping, and great food. READ MORE

King Richard's Faire

Carver—Weekends through October 22, 2023
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. READ MORE

Tales and Tombstones Tour of Salem

Salem—Weekends through October 27, 2023
See the spookier side of Salem in these one-hour nighttime trolley tours past graveyards, haunted houses, underground passageways, and more. READ MORE

Phantoms by Firelight at Old Sturbridge Village

Sturbridge—Weekends through October 29, 2023
This locally 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. READ MORE

Jack-O-Lantern Spectacular

Providence, RI—Daily through Sunday, October 31, 2023
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.  READ MORE

Return of the Pumpkin People

Jackson, NH—October 1 - 31, 2023
Free
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.  READ MORE

Annual Fall Festival at Weir River Farm

Hungham—Saturday, October 7, 2023
Spend time learning about the farm's livestock with educators, climb aboard a tractor, choose a farm “tattoo”, make a spooky mask or a wildflower seed “bomb”, and challenge your friends at corn hole and the potato spoon relay. READ MORE

Berkshire Harvest Festival

Stockbridge—Saturday, October 7 - 8, 2023
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. READ MORE

Mad Love Music Festival

Hingham—Sunday, October 8, 2023
This outdoor festival features local musicians, food, drink, and activities for the whole family. READ MORE

Frightful Fridays at Gore Place

Waltham—Fridays, October 13 - 27, 2023
Take your kids to Gore Place for their annual tradition of spooky (but not too scary) storytelling—strolling through the beautiful 1806 Mansion.  Best for ages 6 and up. READ MORE

Boston Book Festival: Copley Square

Boston—Saturday, October 14, 2023
Free
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.  READ MORE

37th Annual AppleFest at Wachusett Mountain

Princeton—Saturday & Sundays, October 14 - 22, 2023
This all festival celebration includes over 100 craft exhibitors, a farmers' market, kids entertainment, and peak fall foliage viewing from the SkyRide. READ MORE

Sensory-Friendly Boo in the Barnyard

Southborough—Saturday October 14 & 28, 2023
The farm animals love to see you dressed up for Halloween! Halloween activities for children include ghost, pumpkin, and candy corn crafts, mask making, and a special take on trick-or-treating.  READ MORE

The Good Witch of Salem's Halloween Celebration for Families

Salem—Sunday, October 15, 2023
Mark your calendars for a day of Halloween family magic that you won't want to miss! Activities include a Halloween parade, book signing and "spooky"activities. READ MORE

Head of the Charles Regatta

Boston—Friday, October 20 - 22, 2023
Free
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. READ MORE

Stone Zoo’s Boo at the Zoo

Stoneham—Saturday, October 21 - 22, 2023
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! READ MORE

Halloween On The Hill

Beverly—Multiple Dates in October 2023
Explore this beautiful property as they transform Long Hill into a celebration of autumn and the Halloween season. Follow their seasonal-themed trail that will feature over 1,000 jack-o'-lanterns, hundreds of mums and pumpkins, elaborate Halloween sets, light displays, music, and more.  READ MORE

Zoo Howl at Franklin Park Zoo

Dorchester—Saturday, October 28 - 29, 2023
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. Other haunted happenings include mystery animal encounters, costume contests and a scavenger hunt with prizes. READ MORE

Halloween Glow in the Park at TreeTop Adventures

Canton—Saturday, October 28, 2023
Wear a costume and enjoy colored lights and music while climbing through the tree tops on this zip-line obstacle course. READ MORE

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