Fair season in Massachusetts starts in mid-July and ramps up quickly through August. The western half of the state leads the way, with small agricultural fairs that feel more like Vermont than Boston.

July: The Westport Fair (July 15–19) near the Rhode Island border is a classic agricultural fair with oxen pulls, horse shows, and a packed midway. On the same weekend, the Hampshire County 4-H Fair (July 18) in Cummington gives families a small, welcoming introduction to the fair circuit. The month wraps with the Barnstable County Fair (July 20–25) on Cape Cod — one of the few fairs in the state where you can smell salt air from the midway — and the Hampden County 4-H Fair (July 25) on the Big E grounds.

August is peak fair month in Massachusetts. The Bolton Fair (August 14–16) in central Massachusetts is a local favorite — a traditional agricultural fair with demolition derbies, baking competitions, and a strong 4-H presence. The nearby Middlefield Fair (August 14–16) and Martha’s Vineyard Fair (August 13–16) run the same weekend, giving you options from the Berkshires to the islands.

Later in August, the Littleville Fair (August 7–9), Heath Fair (August 21–23), Westfield Fair (August 21–23), and Hardwick Fair (August 21–23) all compete for your weekend. The massive Marshfield Fair (August 21–30) runs for ten days on the South Shore and draws some of the biggest crowds in the state.

The month closes with the Cummington Fair (August 27–30), the Shelburne Grange Fair (August 29), the 3 County Fair in Northampton (August 29), and the Middlesex County 4-H Fair (August 28–30).

For updated information check the websites of the organizing groups or visit Meet Me At The Fair.