Authorities say it happened just before 4 am on N 13 1/4 Road, near W 20 Road in Antioch Township.
The Holland Sentinel reports that Winn was a paraplegic after a 1992 motorbike crash. His wife called him "fearless" saying "he lived his life to the absolute max."
The crash remains under investigation.
Last year there were 16 snowmobile fatalties in Michigan.