This just seems like a natural for Toronto. That is, if we ever get real snow on the ground.
Amsterdam's Pink Christmas, a sort of winter Pride, hosts an
annual Drag Olympics where competitors, kings and queens alike, suit up in eyelashes and parkas and fight for medals in events like the present toss and musical chairs.
The events I would propose for Toronto drag stars would be Running for the Streetcar in the Slush, Riverdale Park West Sledding (extra points awarded to those who can keep their wigs on) and Nathan Phillips Square ice-skating derby, since that's what it feels like skating there already.