After gale-force winds took down most of the fleet in the Mac of 1911, the finish in the 1912 and 1913 races was changed to Harbor Springs on Little Traverse Bay instead of Mackinac Island.

Although the Mac remains primarily an amateur event, this race has a proven track record of attracting some of the finest sailing talent in the sport.

The Mackinac Trophy was won by Providence, owned by Greg and Jerry Miarecki, representing the Chicago Yacht Club.

The Chicago Yacht Club's Ron White won the Martin D. Rieck Trophy for the first multihull to finish in Cheeke Monkey.

The Royono Trophy, given for the first monohull to finish, was won by Peter Thornton's Il Mostro, representing the Chicago Yacht Club.

Infinite Diversion, a Hanse 630e owned by Chicago Yacht Club Commodore Joe Haas, was first to finish in the Cruising Division.

On night of Sunday, 17 July 2011 - during the 103rd running of the race - two sailors died when WingNuts, a high performance keeled sportsboat Kiwi 35, (berthed in Saginaw, Michigan) capsized and turtled in 75 mile per hour winds.

[7][10][11][12][13] WingNuts met then current offshore stability standards, which failed to adequately take into account the effect of the "radical" winged hull.

[5][6][10][11] [B] In the 110th running of the race on July 21, 2018, Jon Santarelli, a 53-year-old sailor aboard the Transpac 52 sailing vessel Imedi slipped overboard during a wave strike approximately 5 nautical miles (5.8 mi; 9.3 km) beyond the start line.

[14][15] On the afternoon of July 28, 2018 - nearly a week after the original incident - his body was recovered by a Chicago Police Marine Unit approximately 6 miles (5.2 nmi; 9.7 km) offshore from Belmont Harbor and identified by the Cook County Medical Examiner's Office as Santarelli.

[16][17][18] The Race to Mackinac is organized and managed by the Mac Committee, a group of active Chicago Yacht Club member-volunteers.

By 2006, with advances in technology and smaller sized components, trackers and race tracking interface using GPS transceivers became standard on each boat.

In 1959, the Island Goats Sailing Society was formed with 10 of these sailors to perpetuate and commemorate the Chicago to Mackinac Race, along with its legends and lore.

"Veteran Chicago-Mac racers have encountered similar conditions during previous races and understand that coping with severe weather is part of the challenge.

Skippers must prepare their boats, train their crew, maintain a watchful eye for approaching storms and "the dearest friend (and most menacing foe) of all sailors -- the wind."