The first official Ulster County Fair was held in 1886, in Ellenville, organized by the Southern Ulster Agricultural Society. The Fair was a boon to the community, bringing visitors from around the county and beyond. Beginning in 1903, the O & W Railroad carried passengers from Kingston and Port Jervis to the Ellenville station, greatly increasing attendance.
From the earliest days of the driving park, a small harvest fair was an annual feature. As the fair grew, agricultural exhibits remained a mainstay of the event. Local farmers brought cattle, pigs and poultry to compete against their neighbors, as well as produce of all kinds. In addition to serving as the location for horse races, baseball games and the Ulster County Fair, the Ellenville Driving Park provided a venue for travelling circuses. Several circus companies visited Ellenville during the late 1800s and early 1900s, including the Walter L. Main Circus, Downie Bros. Circus, and the Ringling Brothers. Another major attraction of the Ulster County Fair was the annual Floral Parade.
After a financially unsuccessful year for the Ulster County Fair in 1931, due to bad weather and a polio epidemic, the fairgrounds were sold the following year to School District 29, and the annual fair was moved to Forsyth Park in Kingston. The fair remained in Kingston until it moved to New Paltz in 1967, where it remains to this day.