1899 - Pittsburgh, Pennsylvania
"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." (Link to Darvarich Affadivit)
This demonstration is not claimed as the first powered flight for several reasons: a) there is no record of the event in terms of speed, altitude or distance measurements; b) it was not a fully controlled flight (as the airplane did not land undamaged); and c) there is very little documentation for this episode beyond the Darvarich affadavit.
1901, Bridgeport Connecticut
The August, 1901 flight was the first of Weisskopf’s flights that was documented and witnessed by neighbours and assistants in addition to being written up in some major publications of the time. On that historic day, at least four flights were reported made, the first before daybreak after a long night of attempting to get the “Bird” to fly. Three more flights were made in the afternoon of the same day, the longest of these was said to have covered a distance of one and a half miles about 200 feet off the ground. These flights were made by the plane that Whitehead referred to as Number 21.
January 17, 1902 - Connecticut
There is more evidence to show that on January 17, 1902, one year and eleven months before Kitty Hawk - two flights were made by Whitehead in a monoplane powered with a kerosene burning engine. Both of these were conducted at Lordship Manor, one lasting a distance of two miles and the other a distance of seven miles over Long Island Sound. These flights were made by Whitehead’s plane – No. 22.
Unfortunately, because Whitehead did not make accurate records of his flight attempts and successes, the distances and heights from the ground are only estimates by witnesses who were present at the flights.
(Incidentally: The Wright Brothers first flights were nowhere near as impressive. The longest flight of three runs made at Kitty Hawk on December 17, 1903 was 59 seconds for 852 feet.)