October GoList: Best Things To Do with Kids in Boston

October in Boston is the greatest. In addition to fall fun like pumpkin picking and the excitement of Halloween, there are country fairs, festivals, special events, and performances galore. Opportunities for families to enjoy the fall foliage during special day or weekend trips are bountiful (and so are the pick-your-own apples at local farms!). Narrowing down our favorite things to do with kids in October is tricky, but here are our top 10 picks; and don't forget to look at our guide to all-free October family activities, too.

Make some feathered friends at the Topsfield Fair. Photo courtesy of the fair

Topsfield Fair - Topsfield
10/4/2019 - 10/14/2019
$10 and up; free for kids under 8
The Topsfield Fair is the quintessential country fair, with traditional agricultural exhibits, big entertainment, rides, games, shopping, and great food (fried Oreos, anyone?).

RELATED: Tips for Going to the Topsfield Fair with Kids

Haunted Happenings Grand Parade - Salem
The annual parade to kick off Salem's Haunted Happenings is filled with color, pageantry, and music. The parade begins at Shetland Park and ends at Salem Common.

RELATED: Mommy Poppins' Guide to the Best Halloween Activities with Boston Kids

Kids will get down to the music at Honk! Photo by Leo March/courtesy of the festival

Honk! Festival - Davis Square, Somerville
10/11/2019 - 10/13/2019
This annual three-day free festival bringing brass bands from all over the United States and the world to Somerville for a celebration of music, community, and activism. Festivities get underway with a lantern parade in Davis Square neighborhoods on Friday night.

RELATED: Boston-Area Fall Festivals You Don't Want to Miss

Opening Our Doors - The Fenway, Boston
Music, theater and dance performances, walking tours, art exhibitions and create-your-own-art opportunities, plus theater workshops for kids and indoor kite flying, are all part of the annual Opening Our Doors Celebration. It is, hands-down, one our favorite annual events in Boston. This is your chance to take the kids to a few of Boston’s finest museums, including the Museum of Fine Arts, Isabella Stewart Gardner Museum, MassArt’s Bakalar and Paine Galleries, and other local galleries. 

Boston Book Festival - Copley Square and Dudley Square
10/19/2019 - 10/20/2019
Boston Book Festival hosts author presentations, panels and hands-on demonstrations at venues throughout the Copley Square area on Saturday and in Dudley Square on Sunday. A street fair in the square on Saturday features exhibitors and live music throughout the day. Activities for kids and teens include everything from costumed story characters to the hottest names in YA literature. 

Outdoor literary fun is a dream for young and old booklovers. Photo courtesy of the Boston Book Festival

Owl Festival at the Blue Hills Trailside Museum - Milton
10/26/2019 - 10/27/2019
Meet live owls up-close and discover how they survive. Celebrate all things owl in myths, legends, and art. Find out about conservation challenges owls face and what you can do to help. There will be kids' crafts, food trucks, and fun for all ages.

Frog Pond Halloween Pumpkin Float - Boston Common
FREE (bring a small pumpkin)
Dress in your Halloween best and bring a small, carved pumpkin to float on the Frog Pond. Kids can decorate a luminary to border the pond, try science experiments, and enjoy refreshments at this urban pumpkin festival.

RELATED: Pumpkin Festivals in New England

Head of the Charles Regatta - Cambridge
10/19/2019 - 10/20/2019
FREE to watch
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. The regatta starts at the Boston University DeWolfe Boathouse and winds three miles upriver to Artesani Playground in Brighton; spectators can watch the races from various spots along the course.

RELATED: Tips for Watching the Head of the Charles Regatta with Kids

Jamaica Pond Lantern Parade - Jamaica Plain
10/19/2019 - 10/20/2019
Imagine wandering around a beautiful pond illuminated by thousands of handmade lanterns. This annual events encourages kids to dress in their Halloween costumes and parade around Jamaica Pond, bringing a trail of bouncing lights into the darkness that can be seen from all directions.

Zoo Howl - Dorchester
10/26/2019- 10/27/2019
Included with Zoo Admission
Celebrate Halloween with the animals at this yearly event at the zoo. There are Halloween-themed games and crafts, plus a haunted maze and zoo animals snacking on pumpkin.

RELATED: Fun Fall Activities with Preschoolers around Boston

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