James Ward-Grist-Miller owned the present village area called Ward's Bridge until 1810, and the land was part of Thomas and Mary Powell's vast farm on both sides of Union Street; they were early Hudson River steamboat builders. From 1850 to 1878, the site hosted the first Orange County Fairs, circuses, sports, and field trips. In 1861, it became part of the farm of Alanson and Elizabeth Hawkins Sears, and was later inherited by their daughter Hannah and George Senior, a prominent merchant. From 1879 to 1920, the Montgomery Driving Park Association held frequent harness racing competitions on a one-half mile track called Pleasure Grounds, where S. Walsh was a notable trainer, driver, and area-wide winner. In 1900, the Community Club of Montgomery Academy alumni promoted village improvements and encouraged scouting events and recreational, educational, local, and county-wide use there. That same year, Charles Tice, a cattle dealer and butcher, kept a livestock yard on the lower 9 acres. Beginning in 1918, Dayton MacMurtrie's large dairy produced Grade A Milk for daily home delivery on the entire farm for half a century. In 1980, attorney Thomas Hadaway purchased the upper track in anticipation of future public works, a police department, and relaxation, and in 1998 residents approved the purchase from a developer of acreage along the Wallkill River for relaxation and recreation.