Stewart Dairy Farm

In 1930, Thomas "Archie" Stewart, an early aviation enthusiast and descendant of prominent local dairy farmer Lachlan Stewart, convinced his uncle Samuel Stewart to donate "Stoney Lonesome", split between the towns of Newburgh and New Windsor, to the nearby city of Newburgh for use as an airport. With the city strapped for cash due to the Depression, however, it was unable to develop it in any way.

Stewart Airfield

In 1934, Douglas MacArthur, then superintendent of the United States Military Academy, proposed flight training for cadets at the airport. The city sold the land to the military academy for one dollar. A small dirt airstrip was cleared and graded. One of the gates at USMA has been known as Stoney Lonesome Gate ever since.

During World War II, many barracks and other buildings, which still stand, were built on the base. In January 2008, the Town of New Windsor received a $2.5 million grant from the state to demolish 30–40 buildings as part of the redevelopment of the former base. First Columbia, the developer, said that 20–30 of the buildings could be retained and reused.

Stewart Air Force / Air National Guard Base

After the creation of the United States Air Force following World War II, the army airfield was converted to an air force base while still being used for training of cadets at West Point. Stewart became the home of Headquarters 1st Region Army Air Defense Command in 1966. It remained so until the deactivation of the Nike Hercules system at the end of 1974. The air force base was deactivated in 1970 and it officially remained unoccupied by the Air Force until 1983, when the 105th Airlift Wing (105 AW) and the 213th Engineer Installation Squadron (213 EIS) of the New York Air National Guard took up quarters. The Air National Guard unit has flown support missions not only for U.S. military operations in Iraq and Afghanistan but also for humanitarian relief efforts.

This area of the airport, now called Stewart Air National Guard Base, was home to the Air Force C-5 Galaxy aircraft before being replaced by the newer and smaller C-17 Globemaster III in 2011. Stewart ANGB also hosted VMGR-452, a Marine Corps Reserve squadron flying the KC-130J, until 2022.

Stewart International Airport

MTA expansion plan

In the early 1970s, Governor Nelson Rockefeller's administration saw the potential for Stewart to support the metropolitan area. Its long runway made it particularly attractive for intercontinental service via supersonic transport (SST), then under development in the U.S. and elsewhere.

The Metropolitan Transportation Authority was the first government body to try to convert it into the New York metropolitan area's fourth major airport. It tripled the airport's territory, extending its land well beyond its previous western boundary at Drury Lane, a two-lane rural road. The state government used its eminent domain powers to take 7,500 acres (30 km2) for terminals, runways and a buffer zone expanding the airport from Newburgh into neighboring towns of Montgomery and a small portion of Hamptonburgh. The land was bounded by I-84 to the north, Route 207 along the south and roughly by Rock Tavern and Maybrook in the west.

Local opposition

Area residents who were already fighting a large power plant proposal at nearby Storm King Mountain fiercely fought the expansion. They took the state to court, ultimately forcing the legislature to write and pass the New York State Eminent Domain Procedure Act, a sweeping overhaul of its existing law on the subject. In order to get the last holdouts off their land, state officials pledged that outside the proposed airport facilities, none of the land taken would ever be redeveloped, a promise that was to haunt them years later.

By the time the land was finally available, the 1973 oil crisis and the attendant increase in the price of jet fuel had forced airlines to cut back, and some of the airport's original backers began arguing it was no longer economically viable. US SST development was canceled in 1971, undercutting another argument for the project. Malcolm Wilson, Rockefeller's successor, put the project on hold; and his successor, Hugh Carey, ended it permanently in 1976.

New York State Department of Transportation ownership

In early 1981, the 52 U.S. hostages held at the former U.S. embassy in Tehran, Iran, returned to American soil at Stewart International following two weeks at U.S. bases in Germany and 444 days of captivity, ending the Iran hostage crisis. The route they took from Stewart International to West Point is marked today as "Freedom Road."

The next year the state transferred control from MTA to its own Department of Transportation (NYSDOT), with a mandate to improve and develop the airport. Three years later W.R. Grace became the first private tenant when it built a corporate jet hangar, and the following year an industrial park was built nearby.