Is This the Earliest?
There is no evidence that natives of the Western Hemisphere knew about kites or kite-flying when Christopher Columbus arrived in 1492. But Columbus had read about Marco Polos travels, which included a discussion of kites, and it is possible some of his sailors had been exposed to them on their voyages to the Middle East. However, there is no substantial evidence of any kiting activity in North or Central America until the 1700s. This excludes Hawaii, which is considered Polynesian.
Shirley Gluboks book Home and Child Life in Colonial Days contains an exhaustive description of games, pastimes, toys and childrens activities in the 1600s and 1700s. The first mention of a kite is in the late 1700s. However, we know Benjamin Franklin flew his famous kite with a key to attract lightning in l752 and also flew kites as a youngster.
In a letter written sometime during 1773, Franklin said to a friend: "When I was a boy...(I) amused myself one day with flying a paper kite, and approaching the bank of a pond, which was near a mile broad, I tied the string to a stake, and the kite ascended to a very considerable height above the pond while I was swimming. In a little time, being desirous of amusing myself with my kite and enjoying at the same time the pleasure of swimming, I returned; and, loosing from the stake the string with the little kite which was fastened to it, went again into the water, where I found that, lying on my back and holding the stick in my hands, I was drawn along the surface of the water in a very agreeable manner. Having then engaged another boy to carry my clothes round the pond, to a place which I pointed out to him on the other side, I began to cross the pond with my kite, which carried me quite over without the least fatigue and the greatest pleasure imaginable....I have never since that time practiced this singular mode of swimming, though I think it not impossible to cross in this manner from Dover to Calais. The packet boat, however, is still preferable."