State police identified the pilots as William Clark, 53, of Matamoras, Pa., and Gary Delia, 61, of Sussex, N.J.
Police said each was flying a single-engine Piper on Monday afternoon when Delia's plane clipped Clark's and they crashed into a wooded area in the Orange County town of Wawayanda, about 60 miles north of New York City.
The men had earlier arrived at Orange County Airport in Delia's Piper Comanche, police said. Clark had been hired to fly a Piper Cherokee back to Sussex County Airport in northern New Jersey. Both men were en route to Sussex when the collision happened, police said.
Investigators from the National Transportation Safety Board were at the crash sites, located about 200 yards apart in a wooded, muddy area about 10 miles north of the New York-New Jersey border, Capt. Joseph Tripodo said.
Delia's plane burst into flames upon impact, while Clark's was crushed, scattering debris over a wide area. Tripodo said police and emergency crews had to use all-terrain vehicles to reach the crash sites.
The plane Clark was flying was owned by Edward Crump, of Boonton, N.J. A message left on Crump's home answering machine Tuesday wasn't immediately returned.
A woman answering the phone at William Clark's home in Matamoras said no one was available and hung up.
Parker Space, a town official in Sussex, told the New Jersey Herald that Delia and another man flew to the New York airport to pick up a plane they were going to work on.
"He loved flying," Space told the newspaper. "It looks like he died doing what he loved to do."