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

Ferris wheel

King Richard’s Faire

235 Main Street, Carver, MA
September 2-October 22 (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!  

Natick Days

Natick Common, 12 South Main Street, Natick, MA
September 8

Natick Days is an annual festival celebrating the community by providing an opportunity for Natick youth groups and non-profit organizations to increase visibility for the great work they do. Festivities include food, fun, and entertainment!

Sterling Fair

Sterling Airport, 121 Greenland Road, Sterling, MA
September 8-10

Head to Sterling to enjoy this family-oriented community agricultural fair! The Sterling Fair features rides, horse pulls, oxen pulls, tractor pulls, helicopter rides, an antique engine and machinery show, livestock shows, food, entertainment, and more!

Chinatown Mid-Autumn Lantern Festival

Boylston Street, Boston, MA
September 9

Enjoy food vendors, street shops, and live performances, including folk dance, martial arts, tai chi, lion dances, and more.

The Big E

1305 Memorial Avenue, West Springfield, MA
September 15-October 1

When it comes to fall fairs near Boston, this is THE one! 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!

South Shore YMCA Corn Festival

South Shore YMCA Emilson Branch, 75 Mill Street, Hanover, MA
September 16-17

The corn festival is a two-day family-friendly event that celebrates the natural and cultural traditions surrounding the fall harvest in New England. Enjoy historical interpreters and storytellers, 4H farm animals, traditional crafts, live music (oldies, bluegrass, folk, country, and more), hay rides, corn maze, pony rides, games, and so much more.

What the Fluff? Festival

Union Square, Somerville, MA
September 23

For one of the least traditional fall fairs in Boston, come celebrate the most delicious confection at the What the Fluff? Festival! Marshmallow Fluff enthusiasts will delight in Fluffalicious Feasts, Flufftastic Fluff Stuff, and frolicking with fellow friends-in-Fluff, making this What the Fluff? the sweetest festival ever!

Faire on the Square

Saltonstall Park, Watertown, MA
September 23

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 23

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.

KidsFest at Wachusett Mountain

Wachusett Moutain, 499 Mountain Road, Princeton, MA
September 23-24

The 32nd annual KidsFest features fun for the entire family. Big imaginations are encouraged! Family fun entertainment throughout the weekend!

Nantucket Island Fair

Children’s Beach, 15 Harbor Way, Nantucket, MA
September 24

This annual family event has all the trimmings of a traditional country fair, with a little island flair thrown in! 

Topsfield Fair

207 Boston Street, Route 1, Topsfield, MA
September 29-October 9

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!

Maynard Fest

Downtown Maynard, MA
September 30

Maynard Fest is an old-fashioned street fair that includes entertainment, family-friendly activities, and more than 120 vendors.

Salem Haunted Happenings

Multiple Locations, Salem, MA
October 1-31

Come celebrate all things Halloween in the spookiest town of them all! Events include a Grand Parade, the Haunted Biz Baz Street Fair, Family Film Nights, costume balls, ghost tours, haunted houses, live music, and chilling theatrical presentations.


1 Davis Square, Somerville, MA
October 6-8

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 14-15

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!

Looking for even more fall fun in Boston? Try a pumpkin patch, a corn maze, or an apple orchard!

Boston Moms
Boston Moms is a rapidly growing community of moms in the Boston area, providing a collaborative parenting resource written and read by local moms. We are passionate about engaging with our readers online through mom-to-mom content + recommendations, and offline through our exciting local events that connect moms to each other and to local and national businesses they should know about!