Race to Mackinac Trophies

The Chicago Yacht Club Race to Mackinac presented by Wintrust is one of the world’s largest annual offshore races, drawing top-notch sailing talent from around America and the world. Known as ‘The Mac’ to everyone in the region, the ultimate test of Great Lakes navigation starts each July just off Chicago’s Navy Pier. Passing through some of the most beautiful coastal waters in the world on the 333-statute mile (289nm) race route, the fleet faces the storms, reefs, calms and competition that truly make it "America’s Offshore Challenge."

From Friday’s Cruising and Saturday’s Racing starting cannons to the finish line just on the other side of the iconic Mackinac Bridge, fans can follow every racer via the live Race Tracker, while keeping tabs on their favorites on Facebook, Twitter and Instagram. Learn more at cycracetomackinac.com.

Trophies recognizing achievements in this race are on display in the cases and on the walls of the Monroe clubhouse. Division and first-to-finish awards recognize the best of the best, awarded for being the winner of their division, or the fastest boat regardless of handicap. Section trophies recognize winners of the individual sections, often consisting of one-design fleets. The Island Goat awards recognize endurance, with a minimum of 25 Mackinac races, and speed, with the fastest goat to the island receiving recognition.

Every trophy has a story and a history, ranging from the Mackinac Cup purchased in 1906, to the series of cups named after geographical landmarks that were added in 2008 for the 100th running of the race. Here you will find photos and histories. But to really appreciate these trophies, take a close look next time you visit the Club.

Division and First to Finish Awards

  • Mackinac Cup—First in Division, Monohull
    • Our grandest trophy, purchased in 1906 by subscription among club members, it is often referred to as “The Canoe”. This was the only permanent trophy for the Mackinac Race until 1927.

      What the various scoring rules were that applied over the years as qualifications for determining the winner has been blurred by the passage of time but the clarity of the engraving recognizing the winners endures. Vencedor, Mistral, Vanadis, Valmore, Malvorneen and Olympian are the classic names of the early winners. Tradition over the years has been for the winner to serve champagne from “The Canoe” to all attending competitors at the annual Mackinac Race awards dinner held in the fall following the race. The days of the winner taking “the Canoe” home or perhaps to their club after posting bond of suitable amount are long over but perhaps this explains some of the minor wear on the vessel.

      Awarding the Mackinac Cup to a single winner simply could not last in the sport of yacht racing. In keeping with the same traditions we follow today, starting in 1927 the Mackinac Cup was assigned alternatively to the Universal (Racing) Division or the Cruising Division of the time. In 1952 the divisions were referred to as the First Division and the Second
      Division, which was determined primarily on yacht size, however, the trophy was alternated as before. Not to leave a simple pattern of alternation alone, in 1971 the Mackinac Committee chose to offer four divisions with no overall award so the Clinch and Ritchie Trophies were called up as division trophies until 1977 when the race reverted to two divisions for most years through 1986.

      As the listing of winners shows, the Mackinac Cup was awarded to one of two divisions on an alternating basis since 1987. Divisions have had various names such as IOR, MHS, IMS, PHRF, Americap, ORR, and even One Design over the recent years. Presently, it is alternated between the larger and the smaller monohull yacht divisions under ORR.

      A trophy so grand could not be without controversy at some point and it did not take but five years to occur. The gale of 1911 which was credited with the sinking of George Tramel’s schooner Vencedor on the rocks off Fisherman’s Island, west of Charlevoix and east of Grand Traverse Light, was a turning point for the Mackinac Race. Faced with criticism of running a race through the more dangerous northerly portion of Lake Michigan including the hazardous practice of cutting the corner at Waugoshance Point, a slim majority of a highly divided board voted to accept an invitation from Little Traverse Yacht Club to run the race to Harbor Springs. This was much to the consternation of then twice Past Commodore Dr. William L. “Billy” Baum who was the last surviving donor of the Mackinac Cup. Billy declared that the Mackinac Cup should not be awarded for a lesser race and that “it should remain on the shelf” until the Mackinac Race resumed. It did. However, the very generous Little Traverse Yacht Club provided an elegant trophy as substitute for the Mackinac Cup for two years of racing to Harbor Springs. Readers are invited to peruse subsequent interwoven chapters of this tale which follow as narratives for the Harbor Springs Trophy and the Warrington Trophy below.

      With a certain amount of artistic license, the Mackinac Cup is fashioned in the shape of a Native American canoe. The detailing is exquisite.

      List of Winners

  • Mackinac Trophy—First in Division, Monohull
    • More formally known from its engraving as the Chicago-Mackinac Trophy but referred to as “The Bowl”, this grand and intricate silver punch bowl was donated in 1927 by Commodore George Woodruff as the second permanent trophy for the Mackinac Race.

      When the Mackinac Race resumed after World War I, it was dominated by the Universal Q Class, and the howl from the cruising boats resulted in the establishment of two divisions along with this very generous donation from Commodore Woodruff. From 1927 to 1951 it was alternated with the Mackinac Cup as the trophy for the Cruising Division or the Universal (Racing) Division. By 1951 the Universal Division of Q’s had dwindled to just 7 boats while the Cruising Division had grown to a then enormous number of 51 yachts. 1952 was the first year of a First Division and Second Division fleet configuration, arranged essentially as the larger boats and the smaller boats. The Mackinac Trophy continued to be alternated between the two divisions until 1971 when the Mackinac Committee chose to offer four divisions with no overall award so the Clinch and Ritchie Trophies were also offered as division trophies until 1977, when the race reverted to two divisions. Designed as a bowl, the Mackinac Trophy has also been used along side the Mackinac Cup for service of champagne by the winners to their competitors at the traditional fall banquet. How the Mackinac Committee explained in 1971 to the division winners of the Ritchie or Clinch Trophies that their trophies did not hold champagne may have been the reason for the reversion to two divisions in 1987.

      The silversmithing of the Mackinac Trophy should not be missed. At the feet of the Native American scouts are turtles, the Native American name for Mackinac Island being “Michilimackinac” or Land of the Great Turtle. Commodore Woodruff provided a complete explanation of the symbols on the trophy in a letter to the club which you can find here.

      List of Winners

  • Manitou Passage Trophy—First in Division, Multihull
    • Purchased by the club in 2008 to provide a division trophy for the multihull fleet, this antiqued punch bowl was selected and named as a reminder of a historically challenging if not perilous portion of the race course that has capsized, sunk, grounded or dismasted both multihull and monohull racers over the years.

      Not to repeat the error of the 1971 Mackinac Committee, the bowl shape of this trophy is functional for the intended purpose of the division winner serving champagne to competitors.

      List of Winners

  • Vanenna Cup—First in Division, Cruising
    • Established in 2008 as the prize for the recently reinstituted Cruising Division, the trophy is named after the winner of the first Mackinac Race in 1898.

      Vanenna was a 64 foot fin keeled sloop owned by William R. Crawford. While not a punch bowl, it is a champagne cooler and is intended to be used by the Cruising Division winner for the purpose of serving champagne to competitors.

      List of Winners

  • Royono Trophy—First to Finish, Monohull
    • Given by John B Ford, Jr. of the Bayview Yacht Club, then Chairman of the Wyandotte Chemical Company and named after his yacht Royono, this large sterling chalice is a testimonial to speed and a bit of frustration. Beginning in 2015, the field in contention for the Royono includes the multihulls as well as the Monohulls.

      Mr. Ford’s Royono, actually Royono III, was first to finish in four consecutive Chicago to Mackinac races from 1946 to 1949 but to the dismay of Mr. Ford, Royono never remained in first place on corrected time. Since 1950 the Royono Trophy has been awarded for “line honors” or simply “getting there first”. Initially, race documents stated it was awarded to “the first yacht crossing the finish line”. As the years rolled onward the trophy was awarded to “the first yacht to finish the race”, a subtle but clear restatement of intent that based “finishing” on elapsed time in recognition of adjustments for staggered starts. No one can recall a year when the “first to finish” was not “first to cross the finish line” but the loophole was closed anyway. In recent years the trophy has been designated with the further clarification as the award or “the first monohull yacht to finish the race”.

      Royono was a 71 foot Alden designed Hereschoff built yawl and a grand yacht in her racing prime. She was later donated in the early 1950’s to the US Naval Academy where she was raced and served as a training vessel. President Kennedy was made aware of her availability and enjoyed a number of sailing excursions on her while in office. Today Royono lives on as a masterfully restored yacht in France on the Mediterranean.

      The winners of the Royono Trophy over the years have been equally interesting, ranging from classic yawls and America’s Cup twelve meters to the high tech design of today’s maxi’s. Size and water line have generally, but not always, held sway. Future winners are not likely to get too much larger than the largest recent contenders as the height of the Mackinac Bridge is becoming a factor with 135 feet of clearance.

      Elapsed times have ranged as widely as the weather on Lake Michigan. Revelry holds the record for the slowest performance at nearly 78 hours in 1955 when the fastest route was up the western shore, over the top of Beaver Island with Lansing Shoal Light to starboard, yes starboard. It must have been very quiet in the Manitou Passage that year and one can only imagine the number of flies. The current record was set by Roy Disney’s Pyewacket in 2002 with a run of 23 hours 30 minutes. This eclipsed the previous record of Pied Piper of 25 hours 50 minutes set in 1987. As further testament to the varied conditions on Lake Michigan, Pied Piper was first to finish in 1996 with a time of nearly 53 hours, more than double the time of her record setting run in 1987.

      List of Winners

  • Martin D Rieck Trophy—First to Finish, Multihull
    • Given in 1998 by Harken to honor fellow colleague and renowned multihull racer Martin D Rieck, the trophy is awarded to the first multihull yacht to cross the finish line at Mackinac Island. From 2015-2017, first to finish award were for the combined monohull/multihull fleets, but beginning in 2018, this trophy was returned to its original purpose.

      Although first awarded in 1999, the list of winners includes information on Steve Fossett’s remarkable record run with Stars and Stripes in 1998. It stands as the fastest time to the Island by any boat and is more than 4 hours faster than the monohull record set by Roy Disney’s Pyewacket.

      List of Winners

  • Ile Aux Galets Cup—First to Finish, Cruising
    • Acquired by the club in 2008 as a Mac section trophy, the cup is named for an island located not far off the rhumb line about eleven miles south of Gray’s Reef.

      Marked by a light, it reminds many that the top of the lake is not too far away. Translated as Bird Island, it’s eastern shoals are particularly hazardous to yachts returning from the race. Starting in 2013, this trophy is awarded to the boat in the Cruising Division with the fastest elapsed time.

      List of Winners

  • Clark - Deroy Trophy—Best Monohull Finish, Bayview & Chicago Macs
    • More fully titled the “Sheldon Clark – Aaron DeRoy Intercity Mackinac Trophy”, this large cast bronze plaque was donated as the award for “the best corrected time per mile in the Chicago to Mackinac and Detroit to Mackinac Races.

      First awarded in 1927 and only a few years thereafter, the incomplete record is an unresolved mystery. Oddly this significant trophy was not referenced in the 1962 or 1976 editions of The Permanent Trophies of Chicago Yacht Club. Sheldon Clark was a Past Commodore at the time the trophy was instituted. Aaron DeRoy was Commodore of the Detroit Yacht Club, a cruising sailor and power boat racer. Awarded in 1987 and again in 2000 as the prize for a Chicago-Port Huron Mac and Port Huron-Chicago Mac respectively, the trophy was returned to its originally intended use in 2006 as its history was rediscovered as the overall trophy for the two Macs. The casting is rich in design elements with iconic architectural images of the time of Chicago, Detroit and Mackinac. One should note that the Bayview Mac never began in Detroit, it would have been a difficult sail up the Saint Clair River. The Trophy Committee welcomes information confirming winners that have not been recognized.

      List of Winners

  • Point Betsie Trophy—Team Challenge
    • Purchased by the club in 2008 for the record number of entries and sections, the trophy was first offered as a multihull section trophy.

      Named for a well recognized Mac Race landmark guarded by a picturesque lighthouse, the trophy is a fluted bowl, handled with lions gripping rings. From 2009 through 2018, it was offered for the “Yacht Club Challenge,” a competition among clubs for the best top finishers. Following a suggestion from the Storm Trisail Club, 2019 brought the introduction of the “Team Challenge.” Self chosen and self named teams of three boats from at least two monohull divisions compete to see who can have the best combined finish.

      List of Winners

Section Awards

  • Harold L. Ashton Perpetual Trophy
    • Given by Nicholas J. Geib in honor of Harold Ashton, long time Race Committee Chairman, for best corrected time in cruising division of the second leg of the Tri-State race sponsored by CYC through 1995.

      Trophy was then dormant until 2004 when it became a Mackinac Race section trophy.

      List of Winners

  • Big Sable Trophy
    • Named after a prominent geographical feature along the race course marked by a distinctive black and white banded lighthouse shining a fixed white light, the trophy was purchased by the club in 2008 as a section award.

      List of Winners

  • George Owens Clinch
    • Presented to the club in 1930 by fellow racing sailor and business associate Archibald McClure Gibson in memory of his good friend George Clinch who served as director and Vice Commodore.

      George Clinch was known for his yachts to be “rigged to stand the gales” and his contention that “cruising boats must stand the gaff while racing boats might stand it” in apparent disdainful reference to the day racers of the time. Signatures of early winners are engraved on the hemispheric portion of the trophy.

      List of Winners

  • Theodore M. Dunlap Memorial
    • Instituted in 1968 in honor of Past Commodore Ted Dunlap.

      It has been a Mac section trophy since inception

      List of Winners

  • Harbor Springs Cup
    • The Chicago-Harbor Springs Cup was presented to the club by Little Traverse Yacht Club in 1912 when a race to Harbor Springs was substituted for the Mackinac Race.

      The winner was the then current commodore, James O. Heyworth, sailing his yawl Polaris. The following year the race was sailed in three separate legs but won again by then past (one year term) Commodore Heyworth on his P Class sloop Olympian. The Race to Mackinac was reinstated in 1914 and the Harbor Springs Cup was dormant until 1940.

      There is more story behind these events. 1911 was the year of a strong gale during the Mac. Vencedor sank after running aground on Fisherman’s Island Reef east of Grand Traverse Light. Great internal dissention ensued regarding the safety of running the Race to Mackinac, especially the dangerous practice of cutting the corner at Waugoshance Point. A highly divided board decided to run a shorter race to Harbor Springs in the face of the threat followed by an invocation of deed restrictions from the then surviving donors of the Mackinac Cup who refused use of the Mackinac Cup for any race not to Mackinac. Seeming to solve the issue of the moment, the Harbor Springs Cup was presented to Chicago Yacht Club as the principal trophy for this new race. The debate continued with accusations about the unchallenging nature of the race to Harbor Springs, fueled perhaps by the two races having been won by Heyworth. Through the efforts of Past Commodore William Baum, the Mac was reinstated in 1914.

      Still more to tell; Little Traverse Yacht Club did not ask for the return of their gift, it sat on the shelf until 1923 when Commodore J. Herndon Smith of Little Traverse Yacht Club sent a clarifying letter stating that Chicago Yacht Club was free to keep the trophy with the hope it would be used in some suitable event. We returned the favor by shelving the trophy until 1940. The Harbor Springs Cup is worth viewing for its engraved scene of Little Traverse Bay and the fine female forms handling the cup. Story over, for now.

      List of Winners

  • James O. Heyworth Trophy
    • In 1940 the daughter and son of Past Commodore James O. Heyworth with encouragement from Commodore Hollis Potter, presented the trophy won by Heyworth’s yawl Polaris in the 1912 Race to Harbor Springs, the substitute for the Race to Mackinac in 1912.

      The trophy had been donated by the Harbor Springs Commercial Club for the race. The trophy has been in continuous use as a Mac section trophy since 1940. We suggest reading the history of the Harbor Springs Cup for the irony.

      List of Winners

  • David W. Howell Memorial
    • Given in 1998 by the widow of David Howell as a Mackinac section trophy, it is the only crystal trophy in the Mackinac Race collection.

      David Howell taught many offshore racers how to sail better, if not as his crew, then as competitors. He was best described as a dominant sailor. His name and the name Decision appear on many trophies.

      List of Winners

  • John D. Kinsey Memorial Trophy
    • Presented to the club by the family and shipmates of John Kinsey in 1968 as a Mac section trophy, the cup is named after a man who was a highly regarded racer, a flag officer, director, and the father of Kay Baxter

      List of Winners

  • Little Sable Trophy
    • Acquired by the club in 2008 as a Mac section trophy, the trophy is named for a point on the eastern shore of Lake Michigan that is often the first landfall for Mac racers.

      Marked by a lighthouse and a sandy shore, it is one of the two “Sables” that mark a legendary easterly boundary of a fast race to Mac.

      List of Winners

  • Ogden Trevor McClurg Memorial Trophy
    • Presented to the club in 1940 by his widow, the trophy has been as section prize since inception. Mr. McClurg was a book publisher and racing yachtsman.

      List of Winners

  • Edward M. Mills Trophy
    • This trophy was donated by Mr. Mills in 1940 as the club expanded its collection of section trophies for the Mackinac Race.

      List of Winners
  • Thomas M. Neill Memorial Trophy
    • Given by the widow of Tom Neill in 2009.

      Tom was one of the club’s most highly regarded and accomplished racing sailors of his time racing a series of boats named Nitemare. The trophy is a C.J. Vander sterling Irish loving cup.

      List of Winners

  • Colonel Robert H. Morse Trophy
    • Donated by Robert Morse in 1928 to be offered for an annual triangular distance race of 60 miles or more.

      This was a course race for a number of years and became a distance race in 1938 to such places as Black Lake, Milwaukee, Saugatuck and later, Waukegan. Since 1977 it has been a Mackinac Race section trophy.

      List of Winners

  • James R. Offield Perpetual Trophy
    • Given in 1956 by James Offield for the winner of the cruising division of the 8-Mile Buoy Race.

      The race was discontinued in 1989 due to the advent of the Verve Cup Regatta. Dormant for a number of years, the trophy has been a Mac section trophy since 2000.

      The trophy is a bronze figure known as Denlillie Havfrue (Little Mermaid) looking out to see in Copenhagen’s harbor. The Little Mermaid, Hans Christian Andersen’s renowned character, was immortalized in bronze by a famous Danish artist, Edvard Ericksen. This sculpture, one of the most famous statues in Denmark, is based on an ancient Danish legend concerning mermaids who welcome sailors who go down with their ships.

      List of Winners

  • Past Commodores Trophy
    • This trophy was presented in 1960 by eleven past commodores who were: Messrs. Potter, Schoenwerk, Metz, Milliken, Sheridean, Danly, Sollitt, Railton, Angsten, Dunlap and Brown.

      The trophy has been a section trophy since inception.

      List of Winners

  • Fred A. Price Memorial
    • The Price Memorial Trophy was presented in 1936 by the widow of Commodore Fred A. Price through the efforts of Commodore Hollis E. Potter.

      This trophy was originally presented to the Lake Michigan Yachting Association in 1910 by Sir Thomas Lipton as a challenge cup. Provisions in the deed awarded the trophy permanently to the first three time winner. William Hale “Big Bill” Thompson, Commodore 1911 and 1912, mayor --- won in 1910 and 1911 with Valmore. Fred Price (Commodore 1920), won in 1912 with Michicago, in 1913 with Olympian but in partnered ownership, in 1914 and 1915 with Valiant. The engraving titling the trophy as the Fred A. Price Memorial Trophy is actually on the back of this silver piece with the Thomas Lipton engraving remaining on the front.

      List of Winners

  • Jack Ritchie Memorial Trophy
    • This silver model of the U.S.C.G. cutter Mackinaw was presented to the club in 1955 by Roy H. Olson as a permanent trophy for the Mackinac Race.

      It has been used for best overall corrected time, as a division award, but mostly as a section award. Robert J. “Jack” Ritchie, Jr. was active as a sailor and member of the Race Committee from 1926 until his death in 1954. Jack served many years as chief observer for the Race Committee on the Mackinaw during races. He was known to have raced Eagle, R and L-16 class yachts. He was one of the few who sailed the Mackinac Race in an R class yacht, aboard Tomboy in 1927. A framed photograph of this trophy was presented in 2006 to the museum on the now retired Mackinaw in Mackinac City, Michigan.

      List of Winners

  • Schooner Trophy
    • Added by the club as a special Mac trophy in 1949, it was awarded to the schooner with the fastest corrected time in the Cruising Division.

      It was won by Happy Holiday five of the first ten years it was offered. Happy Holiday had the fastest elapsed time in 1952 among all early winners at 51 hours 31 minutes and another “winning” time in 1955 of 106 hours 36 minutes when the trophy was also an award for patience. The age of schooners in the Mac came to an end, and the trophy was no longer awarded as there were no eligible entrants. In 1986 it was brought back into use as a section trophy.

      List of Winners

  • Lindy Thomas Trophy
    • Given in 2006 by Lindy Thomas, a veteran offshore skipper, one of the founders of the durable Tartan Ten fleet.

      The trophy is a bronze casting of Round Island Light, the finish mark of the Mac, set on a base of Niagara dolomite, the bedrock of the Great Lakes.

      List of Winners

  • Commodore George Warrington Trophy
    • Presented in 1944 by Chester H. Warrington in honor of his father as a Mackinac Race section trophy.

      George Warrington served as commodore in 1900.

      List of Winners

  • Thomas H. Webb Trophy
    • The Webb Trophy was originally a Columbia Yacht Club trophy for yachts designed to and raced under the Seawanhaka Rule.

      The inscription on the cup states: “Cabin yachts 18 to 30 Feet LWL” and the regatta was traditionally sailed on the 4th of July. From 1901 to 1915 it was won by such yachts as La Rita, Illinois, Spray, and Invader. As was the case in the early days of racing for prizes, a yacht which won the trophy a number of times won the trophy permanently. Such was the case of Leonard J. Lambin with Invader.

      In 1954 Mr. Lambin presented the trophy to the Chicago Yacht Club for use as a permanent trophy in a long distance race. It was awarded for various long distance races run by CYC traditionally over the 4th of July weekend sailed variously to Mackatawa Bay, Milwaukee, Racine, and St. Joseph. After being not-sailed for a number of years, the Webb Trophy has been a Mac section trophy since 2004.

      List of Winners
  • Lynn A. Williams Trophy
    • Given in 1986 by a group of friends, some competitors and some crew, the Lynn Williams Trophy is a model of Dora IV, one of a number of yachts consistently named by Lynn for his dedicated wife Dora.

      Lynn was a true sailing legend, appearing on countless trophies.

      List of Winners

Island Goat Trophies

  • Master Mariner Trophy
    • Given by the families of Dwight Lawrence and Richard Rodseth and the Island Goat Sailing Society, the trophy is an original 1905 section prize mounted on a new base.

      The trophy commemorates those who have sailed 50 Chicago Yacht Club Races to Mackinac. The requirement for membership in the Island Goat Sailing Society is 25 races, thus those who achieve the 50 race level are officially known as “Master Mariners” but also called “Double Goats”.

      List of Winners

  • Fastest Goat to the Island
    • This piece of authentic taxidermy has overseen all conversations in the Mac Bar at Monroe Station since 1970.

      Some of the names on this trophy can only be described as legendary. One will find multiple winners for more recent years as the award was presented to the fastest Island Goat in each division. Through 2009 there has not been a fastest goat declared for the Multihull Division. Perhaps tradition will advance to the Multihull Division in 2010. Not thought suitable for permanent recognition is an annual award presented by the Island Goat Sailing Society for the slowest Island Goat in the race deemed the “Smoked Goat”.

      Beginning in 2015, the award is presented to the fastest goats in the racing and cruising divisions. Also, beginning in 2015, all goats on the fastest boat will be recognized.

      List of Winners

  • Double Goat Recognition Trophy
    • Created in 2008 as a joint effort of the Island Goat Sailing Society and the Society of Mackinac Island Goats, representing “Goating” interests for the Chicago Yacht Club Race to Mackinac and the Bayview Yacht Club Race to Mackinac respectively, this plaque honors those who have completed 25 Macs from Chicago and 25 Macs from Port Huron.

      An identical plaque hangs in the bar at Bayview Yacht Club. This plaque has added a second definition and use of the term “Double Goat”. Since there are not yet any Chicago-Bayview Mac Double Goats who are Master Mariner Double Goats, it is advisable to allow a Double Goat to declare on their own what type of Double Goat they are.

      List of Winners

  • CYC Island Goats Plaque
    • This plaque lists those members of the Island Goat Sailing Society (IGSS) who were members of the Chicago Yacht Club when they joined the IGSS.

      List of Winners

Want to learn more about the Chicago Yacht Club Trophy collection?

contact the Prize & Perpetual Trophy Chair

Email Us
Site Scripts
Hide Click to Edits:
FED Scripts
CWS & Content Load