As a bicycle racer, Western Union bicycle messenger and bicycle shop owner Curtis became interested in motorcycles. He began motorizing bicycles with his own single cylinder internal combustion engines, initially made from tomato cans. In 1903 he set a world speed record for motorcyles by averaging 64mph for one mile. In 1907 he set a new record of 136.27mph, riding a 40hp V8 motorcyle of his own design.
In August 1906, Curtiss visited the Wright Cycle Company and discussed aeronautical engineering with Wilbur and Orville Wright. They did not cooperate, so Curtiss joined with Alexander Graham Bell and others in the Aerial Experiment Association to build aircraft, succeeding publicly in 1908.
In August 1909, Curtiss competed in a Grande Semaine d'Aviation flying contest at Reims, France, organised by the Aero-Club de France. Of 22 pilots, three used Wright Flyer aircraft. On the first day of the competition, Curtiss was sued by the Wright Brothers, who alleged their patent was being infringed. He continued, completing a 10Km course at 46.5mph in just under 16 minutes, 6 seconds faster than runner-up Louis Bleriot.
On May 29, 1910, Curtiss flew from Albany, New York, along the Hudson River, to New York City, to win a $10,000 prize backed by publisher Joseph Pulitzer. He covered 137 miles in 153 minutes, averaging nearly 55mph, then flew over Manhattan Island, and circled the Statue of Liberty, emulating the Wright Brothers' 1909 display there.
The patent dispute continued for several years, closing Curtiss's company, and nearly bankrupting him.