When it comes to annual autumn fair traditions, Connecticans have plenty of options to choose from. In non-COVID-19 years, there are dozens of local fairs held within the state, not to mention “The Big E” Eastern States Exposition located just over the Massachusetts border
in West Springfield. For over 110 years, however, the Danbury Fair was the biggest agricultural attraction in the region, drawing hundreds of thousands of annual visitors from New England and the greater New York City area.
Although agricultural fairs had been held in Danbury since 1821, the Danbury Fair proper first became an organized, annual multi-day event in 1869, when the Danbury Farmers and Manufacturers Society borrowed a tent from the Barnum & Bailey Circus and invited local farmers and crafters to show off their agricultural skills and wares. Over the course of the next several decades, under the leadership of the Leahy family of Danbury, the fair expanded to include nearly 150 acres of both permanent and temporary buildings housing amusement park attractions, races, and traveling shows in addition to agricultural contests, shows, and fair food.
One of the central features of the Danbury Fair was the large oval racetrack at the center of the fairgrounds, where harness races were held throughout the 19th century to the delight of thousands of spectators. In the early 20th century, the annual horse races were replaced with midget car and then stock car racing. During that time, Danbury Fair organizers implemented a variety of creative tactics to drum up excitement and increase visitor turnout for the fair, including purchasing advertising in Times Square, arranging bus transportation from major cities across the Northeast, and even hiring a Theodore Roosevelt impersonator — wearing a Danbury Fair advertisement attached to the back of his jacket — to make appearances at local railroad stations.
After the fair’s charismatic organizer John Leahy died in 1974 with no obvious successor lined up to take his place, the future of the Danbury Fair was thrown into doubt, even as it continued to draw annual crowds of hundreds of thousands of people. When the Danbury Fair opened for the last time on October 4, 1981, it held the distinction of being the oldest continuously-operating annual fair in the United States. Months later, the Leahy family accepted an offer of $24 million for the land comprising the Danbury Fairgrounds, and a few years later, developers built one of the largest shopping malls in the state on the site — named the Danbury Fair Mall.
“The Danbury Fair, 1869-1981,” connecticuthistory.org
Diane Hassan, “The Great Danbury State Fair & Early 20th-Century Outdoor Advertising,” connecticuthistory.org
“Danbury History: Danbury Fair,” Danbury Historical Society