On May 29, 1910, Curtiss flew from Albany to New York City to make the first long-distance flight between two major cities in the U.S. For this 137-mile (220 km) flight, which he completed in just under four hours including two stops to refuel, he won a $10,000 prize offered by publisher Joseph Pulitzer and was awarded permanent possession of the Scientific American trophy.
In June 1910, Curtiss provided a simulated bombing demonstration to naval officers at Hammondsport. Two months later, Lt. Jacob E. Fickel demonstrated the feasibility of shooting at targets on the ground from an aircraft with Curtiss serving as pilot. One month later, in September, he trained Blanche Stuart Scott, who was possibly the first American woman pilot. The fictional character Tom Swift, who first appeared in 1910 in Tom Swift and His Motor Cycle and Tom Swift and His Airship, has been said to have been based on Glenn Curtiss. The Tom Swift books are set in a small town on a lake in upstate New York.
On November 14, 1910, Curtiss demonstration pilot Eugene Ely took off from a temporary platform mounted on the forward deck of the cruiser USS Birmingham. His successful takeoff and ensuing flight to shore marked the beginning of a relationship between Curtiss and the Navy that remained significant for decades. At the end of 1910, Curtiss established a winter encampment at San Diego to teach flying to Army and Naval personnel. Here, he trained Lt. Theodore Ellyson, who became U.S. Naval Aviator #1, and three Army officers, 1st Lt. Paul W. Beck, 2nd Lt. George E. M. Kelly, and 2nd Lt. John C. Walker, Jr., in the first military aviation school. (Chikuhei Nakajima, founder of Nakajima Aircraft Company, was a 1912 graduate.) The original site of this winter encampment is now part of Naval Air Station North Island and is referred to by the Navy as "The Birthplace of Naval Aviation".