Old Drovers Inn dates back to 1750, and was originally opened by John and Ebenezer Preston as the Clear Water Tavern. Here they catered to the traveling desires of the cattle drovers – a group of professional middle men who purchased herds of cattle and swine from New England farmers, drove the animals down the post roads to the New York City markets, and sold the cattle for as good a price as they could get. These New England “cowboys” were a sporty lot who like their rum and who always seemed to have an abundance of ready cash gleaned from their lucrative trade and supplemented from time to time with the rewards of a midnight gathering at the card table. Indeed as their financial prominence became even greater, they hired others to handle the comparatively tedious business of keeping the herds moving while the drovers themselves galloped from Inn to Inn along the route making arrangements and consuming not a little food and drink. The ankle beaters, as the hirelings were called, carried long switches which could be more or less gently applied to the hocks of a slow-moving steer or hog. These were definitely second class citizens in the social order of the drovers, being assigned to sleeping quarters close to the cattle and allowed only an occasional tankard of ale.

The Inn remained in the Preston Family until it was sold to the Potter family in 1910. In 1988 the Inn was sold to Kemper Peacock and Alice Pitcher. Together they brought the Inn to a new level and made the Inn a designation retreat for many Manhattanites and people worldwide. In 1992 the Inn was admitted to the prestigious Relais & Chateaux. Pitcher later ran the Inn with her partner Tom Dott up until it was sold once again in 2005 to a Brooklyn restaurateur. Within five years the business succumbed to a weak economy.