King Richard's Faire
Carver
Ongoing through 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
Campfire Festival
Gloucester
Friday to Monday, September 4 - 7, 2026
Club Passim's Campfire Festival combines the idea of musicians sitting around the campfire playing music with a commitment to developing new talent in the Boston area. Website
Oktoberfest
Walpole
Friday to 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
The Boston Arts Festival
Boston — FREE
Saturday and Sunday, September 12 - 13, 2026
This free annual event showcases Boston's visual and performing arts. Website
Cambridge Carnival International
Cambridge — FREE
Saturday, September 12 - 13, 2026
Cambridge Carnival International is a celebration rooted in African traditions featuring live music, ethnic foods, and crafts from around the world. Website
The Big E
Springfield
September 18 - 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
South Boston Street Festival
South Boston — FREE
Saturday, September 19, 2026
This street festival features “The Best of South Boston,” including over 100 merchants, restaurants, artists, and community organizations, which will fill East Broadway. 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
Rose Kennedy Greenway — 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
RoboBoston 9th Annual Robot Block Party
Boston— FREE
Saturday, September 26, 2026
RoboBoston is a celebration showcasing universities, startups, companies, and student teams with cutting-edge robotics, AI, and technology. This year’s 9th Annual Robot Block Party will include robot demonstrations, hands-on robot interactions, games, and more. Website
Wheels & Wings
Concord, NH— FREE
Sunday, September 27, 2026
There's touch-a-truck, and then there's Wheels & Wings! At this event, kids can climb into and explore trucks AND planes. Website