Lipsner had Miller take off first. In Lipsner’s book Jennies to Jets, he stated that who would lead would be decided by the flip of a coin. Miller went first. He left Belmont Park, New York at roughly seven o’clock on September 5th, 1918, in his Standard JR-1B, tail number 1. However, the weather was not apt to cooperate with the flight. The day was marred by a thick bank of clouds and fog. Despite the poor visibility, Miller successfully flew to the first checkpoint on the flight to Chicago; Lock Haven, Pennsylvania. He arrived at Lock Haven at approximately 10:45. At Lock Haven, he had his plane’s sparkplugs changed. He left Lock Haven, climbed above the cloud cover, and flew in the direction of Chicago.
Or, at least, that is what Miller thought. In reality, the strong winds were blowing him off course. He attempted a decent around an hour later and scraped a tree. This incident was probably due to the difference between the surface elevation of the area he was flying over and the surface elevation of the area he assumed that he was flying over as indicated on his map. Regardless of cause, the result was unchanged, the encounter with the tree left Miller with a leaking radiator.
It is generally agreed upon that he flew on for another fifty or so miles, and attempted to land for water and directions. The accounts on this point, however, differ. One account printed under Miller’s name in an issue of Aerial Age Weekly suggests that he encountered a fair, and flew over it, deciding it to hazardous to land. The other comes from Lipsner’s Jennies to Jets, and states that he did land, he was, however, unable to get water or directions as the farmer that owned the field in which Miller landed threatened him with a shotgun, at which time Miller took off and flew on.
Miller landed in a farmer’s field shortly thereafter, and asked for water and his whereabouts. He got the water and an answer: “Jefferson.” Miller misinterpreted the farmer to mean Jefferson a town in Ohio that was located on the Woodrow Wilson airway (the route that Miller was flying), when, in fact, the farmer was referring to Jefferson County, Ohio. As a result, Miller changed the course, flying in the wrong direction and straying even further from the planned course.
Miller finally realized his error upon landing at an airfield near Cambridge, Ohio. Cambridge was 100 miles south of his destination, Cleveland, Ohio. He immediately headed for Cleveland, stopping several times for water (for his still ailing radiator), eventually arriving in Cleveland at around 9:30 PM. He stayed the night in Cleveland.
The rest of Miller’s trip was relatively uneventful. He left Cleveland at 1:30 in the afternoon, bound for the checkpoint in Bryan, Ohio. Miller stopped for a half hour in Bryan, to refuel landing at around four o’clock. After his brief stay in Bryan he resumed course for Chcago, landing at 7:04 PM to great fanfare.