The 98th annual Race to Mackinac starts tomorrow morning (Sat, July 22, 2006) from the Chicago Yacht Club. The race is sponsored by the Chicago club and they have a ton of race-related photos, videos and information.
You can watch the race online via t2p.tv. If you want to watch the boats pass, Torreson Marine lists some of the best locations on Michigan’s western shore to see them (and also has tons of info and photos from past years all the way back to 1995). The fastest boats typically finish at 30-40 hours and Sunday morning is a great time to see them in northern Michigan.
The online history of the race is scant, but Wikipedia’s entry on the Chicago to Mackinac Boat Race says:
It is one of the longest fresh-water races in the world with hundreds of boats entering the race each year. It starts at Chicago and finishes at Mackinac Island, Michigan crossing Lake Michigan and just entering Lake Huron. The race course runs 333 miles (536 km). 294 boats completed the 2005 race with finishes ranging from 33 to 69 elapsed hours. Steve Fossett set the overall race record, 18 hours, 50 minutes, in 1998 with the yacht, the Stars and Stripes. Roy E. Disney set the monohull record, 23 hours, 30 minutes, in Pyewacket in 2002.