The story of Pillitteri Estates Winery begins generations ago in the heart of old world Sicily. Grape growing was the way of life for the Pillitteri family in Racalmuto. Growing up on the family farm, Gary was soon responsible for helping his father and grandfather with the harvest and the tending of the vines.

In 1948, Gary, at the age of 12, and his father, set off to establish a new life for the family in Canada. They settled in the Niagara area and shortly thereafter were joined by the rest of the family.

In the summer of 1957, Gary was introduced to Lena Agro, a young girl whose family was from the same town in Sicily as the Pillitteri family. On June 18 of 1960, Gary and Lena were married. Their family soon flourished. They welcomed their first born, Connie, on September 23, 1961. They welcomed their second child, Lucy, on February 23, 1963 and they welcomed their third child, Charles, on August 2, 1964.

On December 15, 1965 Gary and Lena Pillitteri settled in Niagara on the Lake to raise their family. They purchased a small fruit farm on Niagara Stone Road. The land was planted to tender fruit (peaches, cherries, pears, plums, prunes, apples, and grapes) and vegetables and in 1973 they opened Gary’s Fruit Market (which actually still operates today in the east wing of the winery).