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I mentioned Detroit/Windsor because it's a common point for Ontario, Michigan, Ohio, Indiana, Illinois, Pennsylvania, and even Quebec. Even coming from Kentucky, Missouri, WV or Minnesota isn't that far on a bike.
May 24 weekend is the weekend of the Rust Revival Spring Thaw in the Red River Gorge of Kentucky.
It's also the first long weekend of the spring/summer and normally when I'm fixing whatever broke at the cottage over the winter (which is why I haven't been at the Spring Thaw for the last 2 years).
I'd be down for a Detroit area get together - super close. But so is Mid-Ohio in July - Lexington Ohio - 3 hours south of Detroit and only 6 hours from Toronto. I haven't made it there yet but would like to (largest swap meet). People already get together for that event.
Events/DTT get togethers I'm aware of:
Spring Thaw Bike Show & Swap Meet in Tennessee - March
Rust Revival Spring Thaw in Kentucky - May
AMA Vintage Motorcycle Days in Ohio - July
Mama Tried/Barber/Ace Corner in Alabama - October
I think I have those right - perhaps we need another thread on this topic and I'll split the posts over to it.