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Leaving Knabenshue, Hamilton returned to balloons through 1907, making ascensions at Battery Park and other points in the New York City area. By this time he was known as one of the most daring parachutists. Not satisfied with one, he developed a stunt of using five chutes, cutting each away in succession until he reached the ground with the last one. 

In May, 1908, Hamilton was back with Knabenshue at Toledo, Ohio, to help fly a new 3-man airship that had just been finished. Following the first tests with Knabenshue, Hamilton and Early Hess on board, they started a tour of exhibitions. During the summer the airship was destroyed by fire in a bad storm at Des Moines, Iowa. Following this, Hamilton purchased an airship and started out on his own. 

In early 1909 he toured Japan and there made a record dirigible flight crossing the Bay of Osaki. This was the first airship ever seen in the Orient and his daring flights were wildly acclaimed. Following his return to the United States Hamilton made flights with his dirigible during the summer months at Brighton Beach, near Coney Island, New York. Reportedly, he first became seriously interested in the airplane when Bleriot crossed the English Channel on July 25, 1909. In August Glenn Curtiss won the Gordon Bennett Aviation Trophy Race at Rheims, France, and this apparently influenced Hamilton's decision to go to Hammondsport about mid-October to see Curtiss about getting into the flying game. He wanted to learn to fly, but this was before Curtiss had started a flying school and Hamilton was informed that there was no plane available, so he could not be taken on as a student. 

With that settled, Curtiss left town on a business trip but Hamilton remained, and very shortly a new plane was completed at the factory and hauled out to the hangar at their flying field. Hamilton watched for his chance and, without consulting anyone, took the plane out alone on October 29th and succeeded in making several short flights before the men at the factory knew what was happening. The next day Hamilton was back at his practice when Curtiss