- 1Topsfield FairTopsfield, MassachusettsEst. 1818October
The Topsfield Fair is one of America's oldest agricultural fairs, established in 1818 by the Essex Agricultural Society — the same year as the Skowhegan State Fair in Maine. Its history stretches back to 1818, placing it among Massachusetts's oldest agricultural fairs. Held annually at the Topsfield Fairgrounds in Essex County, this 11-day fair is a beloved North Shore of Massachusetts tradition drawing hundreds of thousands of visitors each October.
- 2Barnstable County FairFalmouth, MassachusettsEst. 1844July
Every year, Falmouth hosts the Barnstable County Fair, which celebrates Cape Cod's agricultural heritage — one of America's oldest continuously operating fairs (since 1844), it draws visitors from across southeastern New England to the fairgrounds in East Falmouth each July, celebrating a county better known for its beaches and seafood than for its farming. Dating to 1844, it ranks among Massachusetts's oldest agricultural fairs.
- 3Franklin County FairGreenfield, MassachusettsEst. 1848September
Greenfield is home to the Franklin County Fair, which celebrates western Massachusetts' most rural county — the Connecticut River valley's Franklin County is known for its Pioneer Valley farms, tobacco shade production, and vibrant locavore food community centered on Deerfield and the Five College area. Founded in 1848, it stands as one of Massachusetts's most enduring agricultural fair traditions. The fair is one of the oldest in Massachusetts.
- 4Eastern States Exposition (Big E)West Springfield, MassachusettsEst. 1916September
The Eastern States Exposition — universally known as "The Big E" — is the largest fair in New England and one of the top ten attended fairs in the United States, representing all six New England states on a single massive fairground in West Springfield. It began in 1916 and has stayed a fixture of Massachusetts agricultural life for more than a century. Since 1916, the Big E has been the premier fall event of the region, drawing over 1.5 million visitors across its 17-day run.