I've done it. There is certainly some sense of accomplishment riding around the lake and crossing it off a "list" of rides you might have however the ride gets boring on the American side of the lake. I'd suggest riding to Thunder Bay and either circling back and perhaps heading back via hwy11. I don't know what the road over the Kirkland Lake is like but others can comment.
Sleeping Giant park near Thunder Bay is amazing plus there is a nice road into it just watch out for deer.
I would expect it could still be pretty cool in May. You might want to wait until mid June.
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