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9/30/22 - By N Ferreira

Fall is in full swing and the best of October brings outdoor festivities and autumn fun! Sample some of the best 'chowdah' around, 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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Carve out some time for family fun at the Incredible Naumkeag Pumpkin Show. Photo courtesy of The Trustees
Carve out some time for family fun at the Incredible Naumkeag Pumpkin Show. Photo courtesy of The Trustees

Best of October: Top Things To Do in Boston with Kids

Incredible Naumkeag Pumpkin Show

Stockbridge—Friday, September 30 - October 31
Naumkeag's famous gardens in the Berkshires are bedecked with 1,500 jack-o-lanterns, hundreds of mums, and interesting gourds. There will be hot cider and treats. READ MORE

Topsfield Fair

Topsfield—Friday, September 30, 2022 - October 10
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 23
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

Jack-O-Lantern Spectacular

Providence, RI—Daily through Sunday, October 31
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

New Bedford Annual Chowder Festival

New Bedford—Saturday, October 8
The 17th Annual New Bedford Seaport Chowder Festival will have local restaurants and caterers competing for your vote. Sample delicious chowders and soups, and cast your vote for your favorite one. READ MORE

Blue's Cues & You! Live On Stage

Boston—Saturday, October 8
Families can solve Blue's Clues to help Josh put together a magical theater show. This Broadway-style song and dance production invites kids to join in the musical fun as they work with Blue and her friends. READ MORE

Mad Love Music Festival

Hingham—Sunday, October 9
This outdoor festival features local musicians, food, drink, and activities for the whole family. READ MORE

37th Annual AppleFest at Wachusett Mountain

Princeton—Saturday, October 15 - 16
This all festival celebration includes over 100 craft exhibitors, a farmers' market, kids entertainment, and peak fall foliage viewing from the SkyRide. READ MORE

Watertown Fall Festival

Watertown—Saturday, October 15
Savor the beauty of New England in the Fall by carving out some time to connect with friends, and neighbors to enjoy fall activities. READ MORE

Snow White's Halloween Party

Wenham—Saturday, October 15
Put on your Halloween costume or your favorite dress-up clothes and head to the Wenham Museum for stories, songs, and a fun (not spooky) Halloween party for the youngest friends. READ MORE

National Chemistry Week: Fabulous Fibers!

Acton—Sunday October 16
Discover the wonders of chemistry while celebrating National Chemistry Week. Join guest educators from the local American Chemical Society Chapter for fun, hands-on activities around this year’s theme, Fabulous Fibers! READ MORE

Art Ramble: In the Balance

Concord—Daily through Sunday, Nov. 13
Free
The Seventh Annual Exhibition in Hapgood Wright Town Forest features 15 diverse works set up throughout the woods. This year's theme “In the Balance” suggests art in balance with its surroundings, bridging the gap between life's persistence and the loss of habitat. The Art Ramble is both child and dog friendly, so bring the entire family.  READ MORE

Frightful Fridays at Gore Place

Waltham—Multiple Dates
Take your kids to Gore Place for their annual tradition of spooky (but not too scary) storytelling—taking place under a tent on the mansion's sweeping grounds! Best for ages 6 and up. READ MORE

Head of the Charles Regatta

Boston—Friday, October 21 - Sunday, October 23
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 22 - Sunday, October 23
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

Boston Book Festival: Copley Square

Boston—Saturday, October 29
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

Halloween On The Hill

Beverly—Multiple Dates
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 29 - Sunday, October 30
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

Hillside Halloween at the Fruitlands Museum

Harvard—Friday, October 28 - Sunday, October 30
Wear costumes on this trick-or-treating walk on the museum campus and yellow trail. Timed ticketing will allow plenty of space for kids to grab their treats. READ MORE

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