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As a result of this disagreement Herring left and moved to St. Joseph, Michigan, where he continued his work alone.  He had a barn in the back of his house which he kept under rigid lock and key and it soon became known as the "Mystery Barn."  At St. Joseph he was financed by a banker and aviation buff of Elmira, New York, Matthias C. Arnot.  There, in 1898, Herring went ahead and built a glider, or probably what should be called a large flying model, powered by a compressed air engine.  Reportedly it was flown successfully unmanned, then evidently late that year he made several unsuccessful attempts to become airborne himself with this machine from the beach nearby.  It is recorded that Chanute came to St. Joseph to witness these trials.  This power glider was stated to weigh about 90 pounds complete.  Herring continued his experiments there but apparently was out of work and looking for something of financial gain to do.

In early 1902 he was trying to obtain employment with Hudson Maxim on his aviation projects, but was not succussful.  He again approached Chanute about doing more work with his gliders in attempt to beat the reported performance of the Wright brothers at Kitty Hawk.  Evidently Chanute finally agreed to let Herring rebuild one of their earlier multi-wing gliders at St. Joseph and then made arrangements to take it to Kitty Hawk in 1902 at the time the Wrights were there.  Chanute and Herring arrived there on October 5^th with their glider and Herring made his first short glide on the 8th. They remained there until October 14^th but Herring was unable to even approach the work being done by the Wrights. 

Herring lived at St. Joseph until 1904 when he moved to Hempstead, Long Island, New York, to continue his work.  There, in 1907, he entered the competition along with the Wright brothers to supply a plane to the United States Government.  Orville Wright started demonstrating their plane at Ft. Myer, Virginia, on September 3, 1908, but Herring had not as yet 

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