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The land that is now the Thirsty Owl Wine Company was part of a Revolutionary War grant awarded to Sgt. Florence Marony for his courageous service during the American Revolution. The land was then sold to a speculator, John Dunlap, shortly thereafter.
In 1828, 196 acres of the original lot was purchased and maintained by various owners until 1881. That year, the Ditmer family took ownership of the land and remained the sole proprietors for the next 83 years.
In 1964, Bob and Mary Plane bought the land as a summer home. Eight years later, on the advice of Cornell agriculturalists, the Planes began growing grapes to be sold on contract to the Great Western Wine Company. The Planes moved to California in 1980 to learn the wine business and returned later that year, producing six barrels of their first vintage. In 1982 Mary Plane started the Cayuga Wine trail and their winery eventually grew to an 8,000 case production.
In 2002, the Thirsty Owl Wine Company was formed by Jonathan Cupp. His family now carries on the rich tradition of grape growing and fine wine production.