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Best of September 2025: Top Things to Do in Boston
King Richard's Faire
Carver
Ongoing through October, 19, 2025
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. Visit the website here.
Oktoberfest
Walpole
September 6 - 7, 2025
This popular German fest features live entertainment, archery, kids’ games, target shooting, food, and (for the 21+ crowd) beer. Visit the website here.
The Boston Arts Festival
Boston — FREE
September 6 - 7, 2025
This annual event is designed to showcase the visual and performing arts in Boston. Visit the website here.
Cambridge Carnival International
Cambridge — FREE
September 6 - 7, 2025
Cambridge Carnival International is a celebration rooted in African traditions featuring live music, ethnic foods, and crafts from around the world. Visit the website here.
The Big E
Springfield
September 12 - 28, 2025
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. Visit the website here.
Riverfest
Somerville — FREE
September 13, 2025
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. Visit the website here.
Boston Local Food Festival
Rose Kennedy Greenway — FREE
September 14, 2025
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. Visit the website here.
South Boston Street Festival
South Boston — FREE
September 20, 2025
This street festival features “The Best of South Boston” including over 100 merchants, restaurants, artists and community organizations, which will fill East Broadway. Visit the website here.
18th Annual MetroWest Humane Society Craft Fair
Framingham
September 20, 2025
The 17th annual MetroWest Humane Society Craft Fair features vendors specializing in jewelry, home décor, pet toys, candles, and clothing. Visit the website here.
What the Fluff? Festival
Somerville— FREE
September 20, 2025
What the Fluff? A Tribute to Union Square Innovation 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. Visit the website here.
Cambridge Science Festival
Cambridge— FREE
September 21, 2025
A family-friendly science extravaganza, Carnival is a beloved yearly highlight of the Cambridge STEAM calendar! Over 100 activity booths, demonstrations, live music, and installations, including the ever-popular Robot Petting Zoo, come together for one day. Visit the website here.
Fall Family Festival at Bright Horizons
Various locations — FREE
September 25, 2025
Bright Horizons is bringing fun, friends, and family together at their fall festival. Visit the website here.
RoboBoston 8th Annual Robot Block Party
Boston— FREE
September 27, 2025
RoboBoston is a celebration showcasing universities, startups, companies, and student teams with cutting-edge robotics, AI and technology. This year’s 8th Annual Robot Block Party will include robot demonstrations and hands-on interactions with robots, games, and more. Visit the website here.
Wheels & Wings
Concord, NH— FREE
September 28, 2025
There's touch-a-truck and then there's Wheels & Wings! At this event, kids can climb into and explore trucks AND planes. Visit the website here.
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