Wikipedia: Among those who were on hand for the departure of the first flight from Washington, D.C., were President Woodrow Wilson, U.S. Postmaster General Albert S. Burleson, and Assistant Secretary of the Navy Franklin D. Roosevelt. Army Lt. George L. Boyle was selected to pilot aircraft #38262 on the first Northbound flight which, unfortunately, turned out to be a somewhat less than successful initial venture.
Almost immediately after taking off at 11:47AM, Boyle became disoriented and started flying South when he followed the wrong set of railroad tracks out of the city. Realizing that he was lost, Boyle attempted to find out where he was by making an unscheduled landing just 18 minutes later at 12:05PM in Waldorf, Maryland, about 25 miles south of the city. Unfortunately, however, he broke the prop on his airplane when he made a hard landing, so the 140 pounds of mail he was carrying had to be trucked back to Washington from where it was finally flown North to Philadelphia and New York the following day.