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On May 19, 1912, Waite was a passenger with Arch Freeman on a history making flight when they bombed fortifications and little ships over Boston Harbor, on one of the world's first demonstrations of using the aeroplane as a Bombardment Craft. Taking off from Atwood Park at 4:25 A.M., they flew across the marshes to Forts Heath and Banks where Waite dropped several 16 oz. flour bombs in paper bags, hitting buildings and mortar pits. They then flew on to the Charleston Navy Yard where Waite dropped three bombs each on the Battleships New Jersey and Rhode Island at anchor. The flight required 45 minutes and they were back at the Field before full daylight. Their stunt proved surprisingly accurate and drew much front page publicity, but military officers ridiculed the matter saying it would never amount to anything. This was eight years before Billy Mitchell's famed bombing demonstrations. Following this Waite made repeated attempts to interest the Massachusetts National Guard in aviation, but without success.

In June, 1912, Waite purchased Atwood's Burgess-Wright plane, a Model F, No. 20. Reportedly this was the same machine Atwood used when he made his historical FIRST landing on the White House lawn in Washington, D. C. After repeated attempts to get his aviator friends to "check him out" on his own plane, he went at it alone and taught himself to fly. He was very active and during August made 136 flights. Actively continuing his practice, Waite received his license, No. 186, on November 12, 1912, at Cliftondale, Mass. Following this he established the Cliftondale School of Flying at Cliftondale, Mass. to instruct, carry passengers and do exhibition work. There he flew actively during the fall and winter of 1912-1913 and did some instructing. During this period he probably was one of the first to advocate and try to sell the use of the aeroplane for advertising purposes and did considerable early work to get this started.

In the spring of 1913, Waite became an instructor for the Burgess Co. at Marblehead, Mass. where he remained until September 25th of that year, receiving a special letter of recommendation from Mr. Burgess for his excellent flying record. While there he assisted in the training of some of the early Naval aviators. That year Waite was also a Lieutenant in the U.S. Aviation Reserves.

After leaving Burgess, Waite joined the Berger Aviators for exhibition work in the South. He left Massachusetts on October 12th for North Carolina where, on October 14-17 he made 
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