Stewart has a long and varied history that goes back to the earliest days of aviation. In 1930, Thomas Archibald ("Archie") Stewart, an aviation buff and grandson of Lachlan Stewart, a sea captain and lumber merchant who later retired to a dairy farm, had the idea that a city in the 20th century would need an airport to thrive. He persuaded his uncle, Samuel L. Stewart, to donate the original land to the city of Newburgh, and facilitated the transfer of the land to the federal government for $1.
In 1939, the U.S. Military Academy at West Point built the first airfield at Stewart for cadet aviation training, later dedicating it as the "Wings of West Point." In 1948, the airfield became Stewart Air Force Base. It was deactivated and acquired by the state of New York in 1970.
In the 1980s, several business enterprises began operations at the airport after the State Department of Transportation and the Urban Development Corporation began planning for the development of airport land under Stewart Properties.
In 1989, American Airlines announced the beginning of scheduled passenger service at the airport, followed by American Eagle and United Express. That same year, the airport opened its 50,000-square-foot air cargo building, and the U.S. Postal Service opened its new 300,000-square-foot Federal Mail Distribution Facility. On March 31, 2000, SWF became the nation's first privatized commercial airport under a 99-year lease agreement with National Express.
In 2007, the Port Authority took over operations at Stewart and committed $500 million as part of a ten-year capital improvement plan to expand the airport.