The first contracted flight to deliver the mail to this northerly location was widely anticipated as an important milestone, especially among stamp collectors determined to send, then receive back specially marked stamps and envelopes from this historic aerial journey. Interestingly, this created an unusually large volume of mail.

May worked with the pilot I. Glyn-Roberts to complete the task. The first flight was from Fort McMurray to the northern points that included Fort Chipewyan, Fort Fitzgerald, Fort Smith, Fort Resolution, Hay River, Fort Providence, Fort Simpson, Wrigley, Fort Norman, Fort Good Hope, Arctic Red River, Fort McPherson, and finally, Aklavik. The route was 2,697 kilometres down the McKenzie River.

120,000 letters were received for the northerly delivery, the total contents weighing about four tons. To carry such a load, Commercial Airways limited purchased a Lockheed Vega monoplane and two Bellanca cabin monoplanes that were equipped with skis.

There was so much bulk in this first shipment of mail that a series of relay flights were executed, and it took 17 days to make all of the deliveries. Since so many of the collectors had to have their envelopes returned to them for the postmarks to be collectable, most of the load had to be hauled south again.

The irony was that so many envelopes had been circulated on this flight - they were a common item and had little value. An additional irony is that the first airmail delivery to the High Arctic – though not a contracted flight - had already taken place a little under a year earlier, when the aviator Punch Dickins set out on 23 January 1929 to various points in the Arctic Circle.