Biography of the man:

At age 13 Gustave Whitehead and his brothers Nicholas and John were orphaned, so the young Weisskopf worked his way to Brazil as a seaman. He spent four years at sea and showed great mechanical aptitude. A gift well suited for the sea. But his heart was always in the sky. He studied the flight of the sea birds. He also survived four shipwrecks, the last of which put him ashore in 1894 on the Gulf Coast near the Florida Panhandle. Young Weisskopf headed northward, taking work when he could get it and reached Boston in 1897. He got a job with the Boston Aeronautical Society. He built a biplane with flapping midwings, it failed to fly. Next stop was New York City, he met Louise Tuba, they were married in Buffalo, and for a short time Whitehead found employment in a buggy factory at Tonawanda, going from there shortly after the birth of his eldest daughter, Rose, to Johnstown, Pennsylvania. From there, they moved to Pittsburgh to join friends. In the summer of 1900, the Whitehead’s moved into 241 Pine Street in Bridgeport, Connecticut, the address from which many of Gustave's early work was completed. One enigmatic figure in aviation history whose supporters say he made controlled flights as early as 1899 was Gustave Whitehead, a poor, German immigrant to the United States. Whitehead clearly built a number of airplanes before the Wrights were successful in 1903 at Kitty Hawk, but did any of his craft really fly?

First Flight Before the Wright Brothers:

According to an eyewitness account, "In approximately April or May, 1899, I was present and flew with Mr. Whitehead on the occasion when he succeeded in flying his machine, propelled by steam motor, on a flight of approximately a half mile distance, at a height of about 20 to 25 feet from the ground. This flight occurred in Pittsburgh, and the type machine used by mr. Whitehead was a monoplane. We were unable to rise high enough to avoid a three-story building in our path and when the machine fell I was scalded severely by the steam, for I had been firing the boiler. I was obliged to spend several weeks in the hospital, and I recall the incident of the flight very clearly. Mr. Whitehead was not injured, as he had been in the front part of the machine steering it."

Unfortunately there is little information or evidence about the existence of the Pittsburgh flight. The account in Popular Aviation tells us that Whitehead hadn't expected the new airplane to go as far as it did, and he crashed into a building, destroying the craft: But as they went onward and upward, steered by Gustave Whitehead at the controls in the front, they exceeded the distance originally planned and found themselves headed for a three-story brick house. Afraid to attempt to swerve, there was but one hope, namely that they might clear the top of the house. But they failed. Down fell the machine, all but demolished, while the agonized fireman in the back writhed with the pain of a scalded leg. The glasses for indicating water-level in the boilers had broken, permitting steam to envelop the man. Whitehead testing one of the gliders he'd buit. Even the most ardent Whitehead supporters admit that proof of the Pittsburgh experiment is lacking. More evidence is available of the Bridgeport flights, though. The plane Whitehead constructed at Bridgeport was, according to the Popular Aviation article:

...a monoplane with a four-cylinder two-cycle motor located forward. Ignition was of the make and break type and Columbia dry batteries were used. The gas tank was gravity-fed and held two gallons of petrol. The body of the machine was constructed of pine, spruce, and bamboo, reinforced with Shelby steel tubing and piano wires. The wing coverings were of Japanese silk, varnished and fastened to the bamboo struts with white tape. The wings spread out behind the two propellers, and were supported with wires running to a central mast. The entire thing weighed approximately 800 pounds. With Mr. Whitehead aboard the weight was increased to about 965 pounds.