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They would only lose sight of him twice as he stopped to refuel, a challenge Curtiss planned for in advance by reconnoitering suitable landing sites along the route. Among the places he visited were the large, open grounds of the State Hospital for the Insane perched high on a hill above Poughkeepsie. The superintendent, Dr. Taylor, was his escort. As Curtiss later remembered, the doctor chuckled “when I told him that I intended stopping there on my way down the river in a flying machine.”

“Sure you can land here,” Dr. Taylor said. “Most of you flying-machine inventors end up here anyway.”

On the first leg of the flight, high above the Hudson River, Curtiss veered to fly alongside the tracking train chartered by the New York Times. He could see his wife Lena waving her handkerchief and later a large American flag out the train window. Henry Kleckler, too, popped in and out of the train window, nervously flapping his cap. Train and airplane, both traveling at roughly 80 kilometers an hour, wove together and apart along the voyage. As Curtiss remembered, “It was like a real race, and I enjoyed the contest more than anything else during the flight.”

With little instrumentation, Curtiss had no way to determine his speed other than the strength of the wind against his face. With no altimeter, he could similarly only guess at his altitude. And the deafening drone of the engine behind his head shut out all other sound. Nonetheless, he felt in complete control of the airplane and intensely alert to the tiniest details around him on the crystalline day. Below him, groups of people stared from the riverbanks and waved from boats; the captain of a river tugboat tooted its horn. Although Curtiss couldn’t hear it, he saw the blast of white steam rise eerily silent into the air below him.

It was clear sailing until his first stop in an open field just past Poughkeepsie, almost 140 kilometers into his journey, where he greeted assembled spectators and, despite his careful planning, wound up having to borrow gas and oil from generous motorists to get airborne again. Curtiss was soon back above the Hudson. But trouble lay ahead.

Thirty-two kilometers south of Poughkeepsie, the river carves a steep 24-kilometer-long gorge near Storm King Mountain and Breakneck Ridge. The spot funnels treacherous wind currents up from the river. Aware of the danger from his research and reconnaissance, Curtiss tried to climb above it, rising to an altitude of roughly 600 meters. But it was not high enough. Just past Storm King Mountain, as Lena watched frantic and helpless from the train, a crosscurrent tilted the plane sideways, and it dropped more than 30 meters within seconds. Momentarily losing control, Curtiss was nearly thrown from the airplane. “It was the worst plunge I ever got in an aeroplane,” Curtiss said later. “My heart was in my mouth. I thought it was all over.”

As the wind steadied, Curtiss managed to regain control of his airplane. Ahead, he could just make out the northern tip of Manhattan and the outline of the 50-story-high Metropolitan Life Tower-the world’s tallest building-above the line of the horizon. He was beginning to feel elated with the knowledge that he was so near the end of the trip when he noticed that his oil gauge read near empty. The design of the plane required Curtiss to lubricate the engine through a manual control roughly every ten minutes to assure its smooth running; his first thought was that he must have inadvertently “been too enthusiastic” with the oil lever over Breakneck Ridge. In fact, although he wouldn’t discover it until later, the airplane had been seriously leaking oil for some time. With the prospect that his engine could freeze up at any time, Curtiss knew he must land immediately to replenish his oil.

Nervously winging east at the northernmost tip of Manhattan, where the Harlem River curves around at the Harlem Gorge to meet the Hudson, Curtiss looked for a little meadow-one of many such spots he had chosen as possible landing sites. There was no time to lose. Spotting nothing more suitable, he set down on a sloping lawn that rose 30 meters above the Hudson. Safely on the ground, he breathed a sigh of relief and realized that he was inside the city limits. In just over two and a half hours of flying time, he had covered 243 kilometers, averaging nearly 88 kilometers per hour.

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