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L.I., where he gave instruction to Harry P. Whitney on his new plane at the Manhasset Yacht Club.

In the spring of 1916 Webster was again flying for the Burgess Co. and on May 27th he flew over Boston during a Preparedness Demonstration, carrying Carbon Company executive Godfrey L. Cabot as a passenger, on a 50 mile flight. On July 13th Webster and Cabot flew over Nantasket during an M.I.T. graduates' reunion there. Later that same day they flew over Cambridge during dedication ceremonies of some new M.I.T. buildings. In July the Burgess Co. sent Webster to the Naval Aircraft Station at Pensacola, Florida to conduct tests on a new plane before Government officials there. In late July he joined the Massachusetts Naval Militia Aviation Squadron, Marblehead Deck Co. In early August Webster started to instruct Howard S. Borden at Oceanic, N.J. on his new Burgess-Dunne Flying Boat, and while there they made flights over Sea Bright, Long Branch, Asbury Park and various New Jersey resorts.

In May, 1917 Webster became Senior Civilian Instructor at the Squantum Naval Air Station, where he remained until October when he was transferred to Hampton Roads, Va. as Flight Commander. From there he was transferred to Miami, Florida, where he was promoted to Lieutenant (J.G.). In June, 1918 after being transferred to U.S. Marine Corps Reserve as First Lieutenant Naval Aviator No. 112 1/2, he was sent to LaFerne Field, France, where he ferried DH planes from England to France.

Webster returned to civilian life in the United States on April 30, 1919, and entered the U.S. Air Mail Service, first flying from Washington to New York, then New York to Bellefonte, Pa., and Bellefonte to Cleveland, Ohio. In the fall of 1919 he joined the America Trans-Oceanic of New York as pilot, and remained with them and its successor, The Curtiss Metropolitan Aeroplane Co. of Port Washington, L.I. and West Palm Beach, Fla., until 1926. During most of this period he flew to Florida and remained there during the early winter then back to Long Island in the spring. He also did considerable flying to the Bahamas and Havana, his longest trip being from West Palm Beach to Elgin, Ill. via the Mississippi River, in a Curtiss Seagull. While connected with this firm Webster also made a number of noteworthy flights. 

On October 7, 1921 he set a new flying boat record when he flew a new Loening Air