I am probably not the only one to have thought of this, but how about a regatta from Buffalo to Cleveland or Buffalo to Detroit?
What might be really interesting is to have a buoy at major cities on Lake Erie like Erie (PA), Cleveland, Sandusky (OH) or Point Pelee (CA), Toledo then each of those cities would get a tourist attraction as the boats race passed their waterfront.
Plus if all those cities are involved, then sponsors from each of those cities can donate to the prize.
It doesn’t matter whether the race begins in Buffalo or ends in Buffalo though the city where the race ends will certainly get the majority of tourism and media attention [maybe it switches yearly].
No other Great Lakes cities can do it. There are too few major cities on Huron, Superior, Michigan, Ontario. Rochester to Toronto or Toronto to Chicago to Milwaukee wouldn’t be nearly as dramatic. They are only a few miles apart.
I don’t know about anyone else, but does this idea as legs?