20 Can't-Miss September Fairs and Festivals

Staff Writer
Baystateparent Magazine

Three County Fair - Northampton, MA

Labor Day Weekend, Aug. 31-Sept. 3

Classic family fun including animals, acrobats, food, rides and more.

Woodstock Fair - Woodstock, CT

Labor Day Weekend - Aug. 31-Sept. 3

Animal barns, exhibition halls, vendors, rides, and carnival games. Children 10 and under are free.

Gloucester Schooner Festival - Gloucester, MA

Labor Day Weekend, Aug. 31-Sept. 3

Taking place in the harbor and nearby waters of America’s oldest seaport, this festival honors the major role the fishing schooner has played in the heritage of Gloucester and the eastern seaboard. Featuring a parade of schooners on the water and the chance for kids to sail.

Spencer Fair - Spencer, MA

Labor Day Weekend, Sept. 1-3

A timeless country fair including ox and horse pulls, cattle, rabbit and poultry shows, vendors, contests, hall exhibits and performance art. Children under 7 are free.

Appleseed Country Fair - Phillipston, MA

Labor Day Weekend, Sept. 1-3

Three days of live music, food, local vendors, artisans, brewers and the FiddleFest. Kids area features crafts, activities, animals and a rock climbing wall.

King Richard’s Faire - Carver, MA

Weekends, Sept. 1 through Oct. 21

This renaissance-themed attraction features live performances from acrobats, aerialists, fire-eaters, and more.

Franklin County Fair - Greenfield, MA

Thursday through Monday, Sept. 6-9

Named one of the “10 Great New England Fairs” by Globe Magazine, the 170th annual Franklin County Fair proves to be kid-friendly, hosting the first ever Power wheels Demo Derby welcoming 3-8 year olds and a youth/team group trivia challenge on Saturday.

Dartmouth Grange Fair - Dartmouth, MA

Friday & Saturday, Sept. 7-8

Activities include carnival games, judged exhibits, live animals, and more. Admission and entertainment is free.

Sterling Fair - Sterling, MA

Friday through Monday, Sept. 7-9

A two-and-a-half day event filled with agricultural showcases and musical performances. Admission and parking are free.

Mattoon Street Art Festival - Springfield, MA

Saturday & Sunday, Sept. 8-9

In its 46th year, the Mattoon Street Arts Festival is the longest-running street arts show in the Pioneer Valley. The festival features exhibits, food vendors, traveling musicians and more.

Pet Rock Fest - North Grafton, MA

Sunday, Sept. 9

New England’s largest animal welfare music festival, includes a headlining event from platinum-selling singer/songwriter Ryan Cabrera, games for kids, Pups in the Air Frisbee Dog Team, a vegetarian food court, pet contests, a doggie water park, and most importantly, hundreds of nonprofit groups devoted to raising awareness regarding animal cruelty.

Fresh Grass Festival - North Adams, MA

Saturday and Sunday, Sept.14-16

A family-friendly bluegrass festival with over 50 artists and bands, workshops, contests and more, on the grounds of the Massachusetts Museum of Contemporary Art.

Eastern States Exposition (The Big E) - West Springfield, MA

Friday through Sunday, Sept. 14-30

The Big E is the largest fair in the Northeast, offering rides, games, contests, parades, live entertainment and more. Active and retired veterans get in free with proper identification.

stART On The Street - Worcester, MA

Sunday, Sept. 16

Worcester’s Park Ave. plays host to Massachusetts’ largest art, music and performance festival—with over 200 artists. Between perusing the vendors and the vegan food options, watch as local artists create works of art right on the street. Admission is free.

Amherst Poetry Festival - Amherst, MA

Thursday through Sunday, Sept. 20-23.

Hear Emily Dickinson’s poetry and more contemporary work at this festival.

Belchertown Fair - Belchertown, MA

Friday through Sunday, Sept. 21-23

The town common comes alive with rides, food, a petting zoo and more at this traditional country fair.

Team Haverhill’s River Ruckus - Haverhill, MA

Saturday, Sept. 22

Downtown Haverhill shuts down for an afternoon of classic cars, live music, fireworks and a beer garden.

KidsFest at Wachusett Mountain - Princeton, MA

Saturday & Sunday, Sept. 22-23

Two days of live shows, Wachusett Mountains’ scenic summit SkyRide, walk-around entertainment, clowns, magic shows, and more fun for the whole family.

North Quabbin Garlic & Arts Festival - Orange, MA

Saturday & Sunday, Sept. 29-30

Over 100 booths, a main and spoken word stage, and cooking with garlic demonstrations. This festival is waste-free, with most of the waste produced being recycled or turned into compost for local gardens.

Arts in Common - Westborough, MA

Saturday, Sept. 29

The 10th Annual Arts in Common invites artists, performers and neighbors to celebrate the community through the arts.