1898: August 6, 1898, five yachts start in the Race from Chicago to Mackinac Island.
1904: The second Race to Mackinac.
1905: First female skipper Miss Evelyn Wright and her all-woman crew sailed the sloop Lady Eileen. This was also the year of the slowest race; Mistral’s elapsed time was 94 hours, 10 minutes.
1906: The Mackinac Cup is purchased and adopted as perpetual trophy for the annual Chicago to Mackinac race.
1908: William Hale Thompson, Mayor of Chicago, entered his 81 foot racing schooner Valmore and the era of the big schooners started.
1909: For the first time in local yachting history, the story of the progress of the yachts in the Race to Mackinac was reported back to Chicago by wireless telegraph.
1911: Commodore Baum’s Amorita establishes elapsed time record for the Mackinac race, which stood for 76 years at 31 h 14 min 30 sec.
1911: This year, sailors experienced an 80 mph gale. Vendector wrecked on the rocks of Fisherman’s Island off Charlevoix. Thankfully, no lives were lost.
1912-1913: As an aftermath of the 1911 race, several owners favored a shorter race ending in Harbor Springs on Little Traverse Bay.
1914: The Mackinac race resumed on its full course, with only five yachts competing. New racing rules created the P-Class sloop Olympian, which won the race.
1917-1920: Mackinac race suspended during WWI. WWI took away many yachtsmen and put many boats out of commission.
1921: The new Universal rule promoted the P, Q and R class racing yachts and they began to dominate the race.
1924: R-class sloop Sari wins Mac. She was the only R ever to win a Mackinac race and proved that even the smaller sister of the great Ns, Ps and Qs could stand on her own among the Universals.
1925: One of the most grueling races to date, it was a beat to windward practically the entire distance. Only 8 out of 21 starters finished, 6 were driven back to Chicago in the first 12 hours. The Q sloop Virginia won.
1926: Interestingly, the racing rules changed to a minimum of 8 tons, barring Q and R boats from competition, cited as being too small to compete in the big boat race.
1927: The racing rules were changed to allow for 2 distinct classes of boats, and the second Mac cup was created. The Chicago Mackinac Trophy is presented to Chicago Yacht Club by Commodore George Woodruff in 1927 to satisfy the demands of cruising yachts (sloops, yawls, schooners) for a separate trophy from racing yachts (Qs, Ps and other Universal rule type boats).
1933: Chimon becomes the first foreign yacht to win the Mackinac, in from the Royal Canadian YC of Toronto, a schooner owned by Henry K. Hill.
1936: The Mackinac race is grown up. The race saw 42 yachts, representing 13 clubs. More than a third were new boats.
1937: The Year of the Big Blow. The fleet experienced a 65 mph northwester gale; out of a fleet of 42, only 8 yachts finished. George Mergenthaler’s crew on Reverie was rescued by the Coast Guard after being swept overboard.
1946: With the end of WWII, the Mackinac flourished. 1946 saw 53 entries.
1948: L.L. "Ole" Karas wins 9th Mac victory as skipper on Cara Mia, plus his 3 wins crewing a record 62 entries, the fastest race since 1911.
1950: Royono Trophy is established, awarded to the first to finish. The trophy was established after John B. Ford Jr.’s Royono III was the first to finish in four consecutive races from 1946 to 1949, yet was never in first place based on corrected time.
1952: The beginning of the modern era of offshore racing. The Universal division was eliminated. The cruising and racing/cruising divisions were created and eventually became the IOR Grand Prix and the LMYA divisions.
1955: The second slowest race to date since 1898: 77 hours, 52 minutes.
1957: The new Mackinac bridge was erected over the Straits of Mackinac.
1959: The Island Goats Sailing Society is established by Hobart "Red" Olson for sailors who complete 25 races.
1970: Sailors once again experienced a gale, a northerly knocked 45 on the nose for 16 hours, at night exceeding 60 mph and our of 167 starters, 88 withdrew. Ted Turner racing his 12-meter America’s Cup Boat, American Eagle, publicly retracts, calling Lake Michigan a "mill pond."
1979: Island Goats Sailing Society admits its first "nanny goat" (female member) Anne Juell.
1983: MHS and IOR are used as the two rating rules.
1987: Dick Jennings’ Santa Cruz 70, Pied Piper, establishes new elapsed time record for the Mackinac Race – 25:50:44.
1993: Motorola lends 12 Motorola Traxar Global Positioning Systems (GPS) to selected yachts in the race as an experiment in helping the Race Committee track the progress of the race.
1993: Chicago-Mackinac Race commemorative red nun buoy marker erected by Island Goats sailing society and dedicated at Windermere point.
1996: Pied Piper was the first to finish with a time of nearly 53 hours, more than double the time of her record- setting run in 1987.
1996: First time the Mac held an exhibition division for multihulls. In 30 hours, 35 minutes, 28 seconds, Steve Fossett completed the race on Stars and Stripes. Seven multihulls competed in the division.
1998: The Club celebrates the 100th Anniversary of the First Race to Mackinac. A permanent trophy was offered for first overall based on Multihull PHRF handicaps. Also, the Martin D. Rieck Trophy was presented by Harken Marine family and offered by the Mac Committee as the Multihull First to Finish trophy. Steve Fossett set the record this year in 18 hours, 50 minutes and 32 seconds. Multihull record 19 hours, 50 hours, 50 seconds on Stars and Stripes skippered by Steve Fossett.
2000: Real-positioning on 60 boats, at least 3 yachts in each of 20 sections, were equipped with satellite transponders and dedicated GPS receivers that regularly send their exact positions. SailNet got 100,000 website hits as a result.
2002: RaceNet software developed by Microsoft tracks the fleet’s progress throughout the race with real-time scoring functionality.
2002: A cold front shifting northerly broke booms, dismasted one boat, capsized the 44-foot multihull Caliente, caused at least 15 boats to withdraw and set another record. Roy Disney’s Pyewacket breaks the 15-year-old Mac Race record held by Dick Jennings: 23 hours, 30 minutes.
2003: First year for Americap II rating system as sole handicap scoring system for monohulls.
2004: Fifty-five boats use transponders built by SASCO.
2005: Mackinac Committee drafts and launches an online entry and race administration program. Also, Race to Mackinac becomes a true spectator sport as sophisticated GPS transponders are developed by FlagShip IS. Seventy-five boats pilot test new transponders. Three crew members of trimaran Emma near Gray’s Reef.
2005: Record number of website hits: 1.3 million.
2006: Mackinac Committee introduces the Chicago-Mackinac Safety Regulation (CMSR) for monohulls and multihulls. This coalesces ISAF, US SAILING and US Coast Guard safety rules into documents that facilitate and improve compliance. One hundred and sixty boats have transponders. The Chicago Yacht Club Race to Mackinac website and Race tracking site saw over 7 million website hits.
2007: Chicago Mackinac Committee establishes new bonafide division, the Cruising Division.
2008: 100th running of the Race.
2009: Chicago Mackinac Committee establishes new bonafide division, the Doublehanded Division.