The Clipper Cup originated when Jack C. Rillema of Whitehall, MI began having discussions with other sailors on both shores of Lake Michigan relative to the scoring and handicap systems used for the Queen’s Cup Yacht Race.  With the help of Bert Smith in Port Washington, WI, Jack and he established what is now known as the Clipper Cup with the resolve to run a race that was not only FUN but also was clearly scored using the PHRF system.  The race was to run between Port Washington, WI and Muskegon, MI.

In June 1987 the inaugural Clipper Cup race was held.  It ran 68.7 miles originating in Port Washington, WI and ending in Muskegon, MI.  Nearly 90 boats entered the first race.  In 1988 First Chicago Bank became a major sponsor of the Clipper Cup.  About the same number of boats ran the race.  However, concerns began arising with respect to the Clipper Cup and Queen’s Cup being held so close in proximity to one another.  Also there were not a lot of shore side activities within walking distance of the Muskegon Yacht Club as well as dockage being limited.  The organizers changed the course of the race to initiate the start from Muskegon and end at Port Washington.  It became almost the return trip home to WI for many after running the Queen’s Cup.

Although the change resulted in better accommodations and shore side activities there was still concern about the race being run too close to the Queen’s Cup and another new race by the Lake Michigan Single Handed Society’s Double Handed Race that also ended at Port Washington around the same dates.

New chairperson’s Gary and Kate Shottke took over organizing the event.  It was moved to the new Harbor Towne Yacht Club (Gary was Commodore) where there were better dockage options.  During the years it was held at the Harbor Towne Yacht Club several pre-race activities were added including a steak fry and entertainment the night prior to the race.  There was also a pre-race breakfast the morning of the crossing and an option of purchasing box lunches.

In 1997 Bert Smith and the Port Washington Yacht Club took over the helm of the Clipper Cup.  The committee decided to change the race date to the second Friday in August counting on better and warmer weather.  Ten days after the 1998 race Bert Smith sadly passed away.  Organizing of the race has become the responsibility of the Muskegon Yacht Club and has remained strong through the efforts of many volunteers on both shores.

Since its beginning there has only been one year the race has not been held.  In 2012 the race was called due to hazardous weather.  Organizers made the tough decision after keeping in touch with both the Lake Express and Badger ferry companies and them notifying they too were not making their scheduled lake crossings that day.  With safety being paramount to the event the hazardous conditions on both shores were too much.  The next day a modified race between Muskegon and Whitehall, MI was held.

The Clipper Cup is a fantastic event boasting a lot of fun and camaraderie.  There are many special and unique awards, free lunch in Port Washington and a shore side poker run.  In 2014 a $500 raffle was added, it's available to all skippers who finish the race and are present at the award ceremony.  Both host clubs offer warm welcomes with your enjoyment being top priority