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@john_rando @WashedOutGundamPilot @Paultron It will probably be something like this:
Due to the U.S. Neutrality Act planes going to Canada from the U.S.A to help with the war effort could not be flown across the border. This prompted the planes to be flown to the Houlton Air Base and then pulled across the border.
Local tractors and farm trucks were used to pull these planes across the border. Once across, the road would be shut down in order for the planes to take off once again to complete their journey. In this June 2, 1940 photo a farm truck pulled the plane, the border customs building is in the background, and an arrow points to the international border marker.