Contract Air Mail Route 19 - the first Contract Air Mail Route to include scheduled night flying - provided overnight air mail service along the East Coast including four cities with Federal Reserve District Bank offices. The route was segmented into two operating divisions: Northern Division (New York to Richmond) and Southern Division (Richmond to Atlanta). Maintenance facilities and additional aircraft were kept at Richmond (Byrd Field). Contract Air Mail Route 19 connected with Contract Air Mail Route 1 and Contract Air Mail Route 23, unifying Contract Air Mail service between Boston and New Orleans.
Winston-Salem and High Point were officially designated points and were furnished official cachets, although all mail from these two points was flown from Greensboro. There were no point-to-point flights between Winston-Salem, High Point or Greensboro.
A large amount of mail designated for first flight service accumulated at the cities on the route, requiring two aircraft to carry the mail in each direction. Inaugural flights were scheduled so that they could participate in well-publicized route inauguration ceremonies at each airfield on the route. Six pilots flew inaugural aircraft on this route:
Pilot Rutherford Sidney Molloys aircraft was positioned at Greensboro for a route inauguration ceremony. Following the ceremony, Pilot Molloy flew from Greensboro to Richmond with mail intended for Richmond from Greensboro, Winston-Salem, and High Point. From Richmond, he continued along Contract Air Mail Route 19 to Atlanta.
Pilot Amberse M. Banks flew the inaugural southbound flight from New York (Hadley Field, in New Brunswick, New Jersey) in the early evening of May 1 and participated in route inaugural ceremonies at Philadelphia (Municipal Airport) and Washington, DC (Bolling Field). Banks continued to Richmond, where he made an unscheduled flight directly to Philadelphia to retrieve the remaining southbound mail from Philadelphia as well as the southbound mail from Pilot Treat's damaged airplane.
Pilot Verne Egbert Treat flew the second aircraft to depart from Hadley Field after receiving the southbound mail from the Contract Air Mail 1 flight. Treats aircraft flew to Philadelphia, landing in the dark, out of range of the fields floodlights. The aircraft flipped over when its gear dropped into a flooded pothole, damaging the propeller and wings. The pilot and the mail were unscathed, but Treat and his aircraft were unable to continue. Mail from Captain Treats airplane can be identified by an early morning May 2 Philadelphia backstamp.
After Pilot Banks second flight from Philadelphia to Washington, DC, the northbound mail from Pilot Browns aircraft was loaded onto Banks airplane and Banks retraced his route to Philadelphia and New York.
Pilot Eugene R. Brown flew the first northbound flight from Atlanta. His aircraft also carried mail transferred from the inaugural Contract Air Mail Route 23 flight from New Orleans. His arrival at Spartanburg was the feature attraction of the route inauguration ceremonies there. Brown, who arrived at Richmond with northbound mail was then sent to Washington, DC to exchange mail with Banks. At Washington, DC, southbound mail from Pilot Banks aircraft was loaded onto Browns airplane and Brown flew southbound to Richmond.
After the Atlanta (Candler Field) ceremonies concluded, Pilot John S. Kytle made the second northbound departure from there. Kytle arrived at Richmond with northbound mail that was transferred to standby Pilot Morrissey. Pilot Morrissey carried the mail north to Washington, DC, Philadelphia, and New York. The southbound mail from Browns aircraft was transferred to Kytle who returned to Greensboro, Spartanburg and Atlanta.
It was a remarkable feat of rescheduling to solve the problems encountered during the inaugural night. All of the mail in both directions arrived before banks and commerce opened for business on May 2.
Official cachets were furnished all points by the Post Office Department. Although the official cachets prepared for the route show the date as May 2 1928, inaugural flights were made on May 1 from every airfield on the route except southbound from Greensboro and Spartanburg and northbound from Richmond, Washington and Philadelphia. Many cities applied the official cachet in multiple colors. The Philadelphia cachet exists in orange, caused by use of ink eradicator.
The Philadelphia cachet exists without the words Philadelphia, Pa., although most covers from this point bear cachets with the city name. The Richmond Post Office applied a supplemental cachet on the back of some covers.
Scheduled service on the 748-mile route was one daily trip each way except on Sundays. Pitcairn Airways had eight Pitcairn PA-5 "Mailwing" biplanes specifically designed as mail planes for night flying operations.