Boston Moms Guide to Fall Fairs and Festivals

It’s fair and festival season in Boston! Pack up the family for a day of good old-fashioned fun, and head to the FAIR! 

Ferris wheel


The Big E

1305 Memorial Avenue, West Springfield, MA
September 16-October 2

For 17 days you can experience everything a state fair has to offer! Concerts, concessions, rides, agricultural shows, a circus, crafts and vendors, and so much more!

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Topsfield Fair

207 Boston Street, Route 1, Topsfield, MA
September 30-October 10

Come take part in the 38th annual giant pumpkin weigh off, cheer for the demolition derby, catch some great live entertainment, ride some rides on the midway, and check out the amazing crafts at the Topsfield Fair!

King Richard’s Faire

235 Main Street, Carver, MA
September 3-October 23 (Weekends Only)

Visit the eight stages, watch a jousting tournament, and enjoy tons of street entertainment and performances! Come in costume or not. There is so much to do, you may want to come back for multiple days to experience it all!  

Fall is my favorite season. I love everything from the crisp leaves to pumpkin spice to apple picking. But the fall tradition my family loves most of all? Visiting King Richard’s Faire in Carver! Renaissance faires are a great venue for...

Nantucket Harvest Fair

Milestone Cranberry Bogs, 220 Milestone Road, Nantucket, MA
October 1-2

New for 2022, the Nantucket Conservation Foundation’s Cranberry Festival has joined forces with the Nantucket Island Fair to create something that captures the spirit of both events and brings this important family-friendly celebration back to the “shoulder season.” These two fall fairs are beloved, historic island events!

Faire on the Square

Saltonstall Park, Watertown, MA
September 24

Kids can get their faces painted, jump in bouncy houses, ride a pony and so much more at this family friendly festival! Grab a delicious bite to eat from one of the many food vendors, shop local crafts, and take in a live show on the main stage!

Mystic River Celebration

Condon Shell, 2501 Mystic Valley Parkway, Medford, MA
September 24

Support local artisan crafts, eat amazing food, enjoy live performances by local talent, and enjoy fun activities for all ages, including a Knucklebones play area for kids! This event is the kick-off to Arts Across Medford, CACHE’s month-long arts festival during October.


1 Davis Square, Somerville, MA
October 7-9

Come for the music, make some art, march in the parade, build community, and stand up for social justice — all for free! There will be a Friday evening HONK! showcasing bands of particular interest, free performances and art-making activities all day Saturday, and the ever-popular Sunday HONK! parade down Massachusetts Avenue, which will be followed by a full afternoon of HONK! performances in Harvard Square!

37th Annual AppleFest at Wachusett Mountain

499 Mountain Road, Princeton, MA
October 15-16

Come celebrate all things fall with live music, apple pie baking and eating Contests, 100 craft exhibitors, a farmers’ market, kids entertainment, and amazing views of the fall foliage from the SkyRide!

Meghan was born and raised on the South Shore and attended college in Boston. After college, she married her high school sweetheart and followed him to Charleston, SC, and Groton, CT, where he served as a submarine officer in the United States Navy. Military life was an adventure, and after six crazy years of service (and two babies later!), the pair decided to move *home* to the South Shore in 2016 and put down some roots. Meghan is the proud owner of Boston Moms and work-at-home mom to William, Benjamin, and Caroline, born in 2013, 2015 and 2019. She loves meeting new people, encouraging moms, celebrating motherhood, and supporting small businesses.