Paumanok Vineyards, on Long Island's bucolic North Fork, was founded in 1983, making it one of the oldest producers on the island. In the early 1980s, Charles Massoud, a former IBM executive, and his wife Ursula heard about the East End and its burgeoning wine industry. By 1983, they were intrigued enough to buy an old potato farm in Aquebogue and plant it with about 15 acres of grapes. In a spirit of romanticism, they named both the winery and the vineyard Paumanok, after the original name for Long Island, as made famous by the American poet, Walt Whitman.

Eventually, Paumanok Vineyards grew to a total of 60 acres and in 1991 the Massoulds sold their first wine. By 1992, IBM was offering generous buyouts and the demands of the winery were getting bigger. Charles took early retirement, although he laughingly refers to his package as a “bronze parachute,” because “it was not quite gold where I was.” The Massouds then moved full time to the vineyard from their Stamford, Connecticut home.

Since then, the Massouds have run Paumanok as a family, with Charles serving as winemaker. That is, until recently, when his eldest son Kareem started making the wines by his side. Many local wineries say they are "family" operations, but this is particularly apt in the case of Paumanok, where the Massouds do most everything and Kareem has the honor of being the Island's first second-generation winemaker.