The first experimental flight carried out by the Association took place on 6 December 1907. The test aircraft, piloted by Selfridge, was a large, tetrahedral kite placed on pontoons called the Cygnet I. The kite was pulled by the steamboat Blue Hill on Bras’Or Lake, Nova Scotia. Cygnet I reached a height of 51 metres and remained in the air for seven minutes, but when it landed on the lake the towline was not released and the kite with Selfridge was pulled below the water’s surface. The kite was destroyed and Selfridge was rescued.

The development of additional flying machines moved to Hammondsport, New York because Curtiss had his machine shop there.

The first machine built by the Association was called the Red Wing because of its colour. The first engine Curtiss designed specifically for aircraft was used in the Red Wing. Casey Baldwin successfully flew it on 12 March 1908 for 97 metres. His second flight took him 37 metres, but ended with heavy damage to the aircraft. The Red Wing had no controls except an elevator (a control used to adjust the up and down motion, or pitch, of an aircraft's nose or tail), and it was this lack of control that led to its destruction.

The next aircraft was named the White Wing, and the members of the Association developed controlled flaps on the wings that improved stability. These control flaps were soon called ailerons by another well-known aviation pioneer, Hari Farman.

The White Wing was flown four times in 1908: first by Baldwin on 18 May for 82 metres, Selfridge on 19 May for 73 metres, Curtiss on 20 May for 310 metres, and finally on 23 May by McCurdy, who flew for 183 metres, landing with a destructive crash that slightly injured the pilot.

The Association’s next aircraft was the June Bug. It was flown many times between 21 June and 31 August, with the longest flight lasting over three kilometres. When it was flown by Curtiss on 4 July 1908, it set the record for being the first aircraft to fly one kilometre in the western hemisphere, and received the Scientific American Trophy.

The June Bug was renamed The Loon in November when members of the Association put pontoons on it to experiment with flight off water surfaces, but the experiment ended in failure.