There is a distance paddling/sailing event called the Tip of the Mitt (Michigan) Challenge. The course (300 miles) is from Oscoda (Lake Huron) to Manistee (Lake Michigan) through the Mackinac straights. I know of a Wayfarer (with a crew of 2) who did the event last year. There is also a 150 mile (shorter) course from Michigan City to Manistee. You can find out more about these events at:
There have also been a selection of regatta events/resources posted to the SailMichigan.org (Sail Michigan | Online Database of Sailing Lakes in Michigan | SailRatings™
I think I may look seriously into these events myself.