The Oldest Fairs in Connecticut

The Brooklyn Fair is one of the oldest continuously running fairs in America, celebrating over 215 years of agricultural tradition in northeastern Connecticut. Dating to 1809, it is one of Connecticut's oldest and most enduring agricultural fair traditions. Organized by the Windham County Agricultural Society, this beloved fair draws visitors from across New England for a long weekend of authentic rural New England fair traditions.

The Harwinton Fair is a beloved autumn tradition in the Litchfield Hills of northwest Connecticut, having celebrated its 169th year in 2026. Dating to 1857, it is one of Connecticut's oldest and most enduring agricultural fair traditions. This three-day fair at the Harwinton Fairgrounds brings together the agricultural communities of Litchfield County each early October for competition, entertainment, and New England fall traditions.

The Woodstock Fair is Connecticut's largest agricultural fair and a Labor Day Weekend institution in the Quiet Corner of northeast Connecticut. Dating to 1860, it is one of Connecticut's oldest and most enduring agricultural fair traditions. Held since 1860 at the Woodstock Fairgrounds, this five-day fair celebrates the pastoral traditions of the Woodstock and Windham County communities with some of the best livestock competitions in New England.

The Durham Fair is Connecticut's largest agricultural fair by attendance, drawing over 150,000 visitors each year during the last full weekend of September. First held in 1916, it has been a Connecticut agricultural tradition for over a century. Organized by the Durham Agricultural Society, this four-day fair has been a Connecticut institution for over a century, showcasing the best of New England agriculture and rural tradition.