NJ Trail 24 Hour
I'm not much of a competitor, but this sounds like fun.
With careful thoughtful planning this seems possible.
I did the NJ lighthouse tour 2 years ago. Lots of people take a weekend to do it. My wife and I completed the circuit on Sunday, starting at the Sandy Hookk lighthouse as they opened and just making it to the last lighthouse before they closed, then another 85 miles home.
And we were on a borrowed Electra-Glide. Was really a fun day.