The first Chicago Yacht Club Race to Mackinac was held in 1898 as an informal race of five boats, and Vanenna won in 51 hours. It was six years later before the second Mac ran in 1904, after which it was then held intermittently until after World War I. Since 1921, the Mac has been a highly-anticipated annual event not only by the Chicago Yacht Club immediate family but is also revered by the extended racing community and by the City of Chicago.
The Chicago Yacht Club Race to Mackinac is a 333 statute mile (289.4 nautical miles) course starting just off Navy Pier and ending at Mackinac Island, Michigan. It is the oldest annual freshwater distance race in the world. The boats cross the finish line between the lighthouse on Round Island and Windermere Point on Mackinac Island. Recently the race has had about 330 yachts of various sizes and sections including a cruising class, multi-hull, double handed, and many one design sections. The race is by invitation only.