October GoList: Best Things to Do with Kids in Boston

family things to do in boston in october

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. Here are our top 10 picks this October.

Root for the swiftest (and cutest) piglet at the Topsfield Fair.. Photo courtesy of the fair

Topsfield Fair - Topsfield
Through 10/8/2018
$10 and up; free for kids under 8
The Topsfield Fair is the quintessential country fair: traditional agricultural exhibits, big entertainment, rides, games, shopping, and great food.

Haunted Happenings Grand Parade - Salem
The annual parade to kick off Salem's Haunted Happenings is filled with color, pageantry, and music.  Groups of Salem kids from preschool to college celebrate this year's theme of "Movie Monsters." The parade begins at Shetland Park and ends at Salem Common.

Jack-O-Lantern Journey - Franklin Park Zoo, Boston
10/5/2018 - 11/4/2018
Walk along a half-mile, tree-lined trail at the Franklin Park Zoo to see more than 5,000 pumpkins carved into designs based on prehistoric creatures, sea life, and even endangered species. Open at dusk after the zoo closes for the evening, the trail ends with pumpkin carving demonstrations and seasonal treats. See our post for even more carved pumpkin displays.

Boogie down with brass bands in Harvard Square. Photo by Leo March/courtesy of the festival

Honk! Festival - Harvard Square, Cambridge
10/5/2018 - 10/7/2018
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.

Opening Our Doors - The Fenway, Boston
Music, theater and dance performances, walking tours, art exhibitions and create-your-own-art opportunities, plus theatre 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, Boston
Boston Book Festival hosts author presentations, panels and hands-on demonstrations at 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. Activities for kids and teens include everything from costumed story characters to the hottest names in YA literature. 

Owl Festival at the Blue Hills Trailside Museum - Milton
10/13/2018 - 10/14/2018
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 kid's crafts, food trucks, and fun for all ages.

Pumpkins, ahoy! Photo courtesy of Boston Common Frog Pond

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 local pumpkin festival.

Head of the Charles Regatta - Cambridge
10/20/2018 - 10/21/2018
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.

Jamaica Pond Lantern Parade - Jamaica Plain
10/20/2018 - 10/21/2018
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.