Fall Festivals for Kids in Boston in 2026
King Richard's Faire
Carver
Weekends, September 5-October 25, 2026
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. Website
Oktoberfest
Boylston Schul-Verein, Walpole
Friday - Sunday, September 11-13, 2026
This popular German fest features live entertainment, archery, kids’ games, target shooting, food, and (for the 21+ crowd) beer. Website
Riverfest
Somerville — FREE
Saturday, September 12, 2026
Riverfest is the culmination of a summer of activity at Assembly Row with live local music, dozens of local artists, free children’s activities, a sidewalk sale, and of course the annual fireworks show over the Mystic River. Website
Faire on the Square
Watertown — FREE
Saturday, September 19, 2026
The Faire offers a wide variety of free activities for children and adults including children's rides and activities, musical entertainment and food, crafts sales, and dance performances. Website
What the Fluff? Festival
Somerville — FREE
Saturday, September 19, 2026
What the Fluff? is a lively festival celebrating the invention of Marshmallow Fluff and Somerville’s legacy of creativity. This year will feature live music, fluff-filled feasts, fun games, and zany activities. Website
Boston Local Food Festival
Boston — FREE
Sunday, September 20, 2026
The Boston Local Food Festival, overlooking historic Boston Harbor, is an outdoor, beginning-of-autumn celebration of the many virtues of locally grown and produced food. Website
Harvest Fest at Southwick's Zoo
Mendon
Saturday, September 26, 2026
Celebrate the beauty of autumn at Harvest Fest, a seasonal celebration at Southwick’s Zoo filled with live entertainment, local artisan vendors, and festive fall fun. Website
HONK! Festival
Somerville — FREE
Saturday, October 10, 2026
One of the Boston area's most colorful fall traditions brings activist street bands from around the country to Somerville and Cambridge for an afternoon of music, dancing, community events, and wonderfully unconventional performances. Website
Newton Harvest Fair
Newton — FREE
Saturday & Sunday, October 17 & 18, 2026
For over 40 years Newton has celebrated the change of seasons and gathered as a community at the Harvest Fair in Newton Centre. Website
Annual AppleFest at Wachusett Mountain
Princeton
Saturdays & Sundays, October 17 - 25, 2026
Wachusett Mountain’s 42nd annual AppleFest is the ticket to both, featuring every apple-flavored treat from candy to cocktails, and one of the most unique bird’s-eye views of Fall foliage in Massachusetts. Website
Fall Festivals Worth the Day Trip from Boston
The Big E
Springfield
Friday, September 18 - Sunday, October 4, 2026
The Big E, or Eastern States Exposition, is a New England autumn tradition and the ninth-largest fair in North America. The Big E features entertainment, major exhibits, The Big E Super Circus, the Avenue of States, and dazzling thrill shows. Website
Vermont Pumpkin Chuckin' Festival
Stowe VT
Sunday, September 27, 2026
Stowe Vermont's 17th annual festival of pumpkin catapulting features live music, food trucks, children's activities, and a chili cook-off among area restaurants. Website
Topsfield Fair
Topsfield
Friday, October 2 - Monday, October 12, 2026
The Topsfield Fair is the quintessential country fair - traditional agricultural exhibits, big entertainment, rides, games, shopping, and great food. Website