Updated: Apr 21, 2020
We love fall's stunning blue skies, crispy apples, crunchy leaves, and wealth of festivals and fairs in and around Boston. Here are a few of our favorites:
Topsfield Fair, September 29–October 9, Topsfield
A celebration of agriculture, entertainment, and food, this fair is a must if you can get out there. Beautiful animals, great music, rides and games, and of course, lots of food on a stick. One of our favorite parts of the fair is the Giant Pumpkin weigh-off…last year’s winner weighed 2075.5 pounds! $9 if you buy your tickets now, $11-$15 after the fair starts.
HONK! Festival of Activist Street Bands, October 6–8, in and around Davis Square, Somerville
An awesome annual 3-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. The festival kicks off on Friday night with a lantern parade in Davis Square neighborhoods and a band showcase. On Saturday more than 25 bands take over Davis Square for a giant music and dance party. On Sunday, local community groups, artists, and activists working for a variety of progressive causes—economic justice, protecting the environment, world peace, an end to racism—join the brass bands to make a spectacular parade from Davis Square to Harvard Square along Mass Avenue.
Cranberry Harvest Celebration, October 7–8, Wareham
The Cranberry Harvest Celebration is a great way to see and learn about the picturesque cranberry harvest while enjoying some old fashioned family fun. Watch the harvest of the crimson berries, visit educational and historical displays, view the spectacular landscape and harvest by taking a helicopter ride, enjoy live cooking demonstrations by some of the area’s finest chefs and culinary professionals, shop the marketplace with over 40 juried exhibitors from around the region, listen to local musicians, and peruse the farmers' market and food concession areas for the best fare around. Returning this year, you can put on a pair of waders and stand in a bog full of cranberries! Children’s activities include pony, paddle boat, train, live entertainment, wagon rides and much more.
Arlington Open Studios, October 14, 12:00–5:00 pm, Arlington Join the Arlington Center for the Arts for our new-format, new-location, one-day only Arlington Open Studios Arts and Artisan Festival in the heart of Arlington Center. All mediums encouraged, including painting, photography, fiber, ceramics, glass, fine jewelry, mixed media, printmaking, sculpture, artisanal food, writers & poets, musicians and makers of all kinds!
Wellfleet OysterFest, October 14–15, Wellfleet
The Wellfleet OysterFest is an annual celebration of the town’s famous oysters, clams and its deep-rooted shellfishing traditions. Wellfleet’s town center comes alive for this two-day family festival that brings together locals and visitors for a weekend full of food, art, music, storytelling, cooking demonstrations, nature walks, and more.
Head of the Charles Regatta, October 21–22, Cambridge
Entering its 53rd year, the Head of the Charles Regatta has grown to become the premier two-day rowing event in the world. More than 11,000 athletes from around the globe compete in 56 different race events, attracting tens of thousands of spectators each year. Food and souvenirs are available for purchase.