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Reuben Leonard operated several businesses in Leonardsville soon after 1800; among them was a grocery and dry goods store. Before the establishment of a government post office, it was custom to address mail to the recipient "In care of Leonards." When the Post Office Department eventually gave this location an official name, it was Leonardsville. Although Leonardsville received its name from Reuben Leonard, it owes its existence to "The Shops," as the various small manufactories of the last century were called.

Located on the Unadilla River, where a dam provided water power, a scythe and hoe factory was in business by 1808. Other factories which gained their power from the impounded water included a general blacksmith shop, grist and saw mills, a horse rake factory and wagon shop, a foundry and machine shop.

In 1856, the grist mill, saw mill and agricultural implement factory were destroyed in a spectacular fire, but they were rebuilt at once. The Babcock family soon acquired and operated the business for about 75 years, sometimes employing over 100 men and exercising great influence over village economy. The "Shops" finally closed in the 1950s, soon followed by the Unadilla Valley (Dilly Dally) Railroad, the milk station, the feed store, and other small mercantile establishments. None of the manufacturing buildings of the town remain.

The Leonardsville High School graduated its last class in 1969 when the district merged with Bridgewater and West Winfield. The Building served as an elementary school until its closure in 2001. It is still owned by the district and used for specialized educational programs.