I don't think slower piston-driven-engine planes flew high enough to leave contrails.
Anybody

I have a sort of memory of contrails behind the Lockheed Super-Constellations in the late fifties/early sixties. But I may be wrong, there. By that time, there were jet airliners flying around, as well as military stuff, so I may have got mixed up.
(Although I do have to say that I was pretty hot on aircraft recgonition in those days.)