This weekend marks the annual intersection of sailing, beer drinking and charitable giving, a mix more harmonious because it is set on the shores of Lake Michigan, in the beer capital of America — Milwaukee, Wisconsin. A group of the city’s sailors in 1999 basically wanted one more sailing regatta before they had to pull their boats from the water and turn their attention to snow shovels. The eager yachtsmen staged Louie’s Last Regatta, a charity event which raised $900 for the Children’s Hospital of Milwaukee. Just 12 boats participated. In 2006 the regatta raised over $123,000 and filled the sails of 131 registered boats. Louie’s Last Regatta continues to grow, its beer-can-shaped race coarse becoming one of the largest single charity regattas in the nation.
In 2004 SAILING Magazine honored Louie’s Last Regatta as one of the Top Ten Best Sailing events in the country. It is no wonder. The history of Louie’s is as colorful as the man for whom the race is named. And every year, Children’s Hospital benefits. From the silent auction, to outright bribery by captains for charity, from hand-crafted works auctioned online, to donations from major sponsors, Louie’s has become a legend in the American sailing community.
The post race party is held waterside at the Milwaukee Ale House. The event gained its name from the Ale House’s flagship brand, “Louie’s Demise” Amber Ale. The story goes that Louie Eishold, a great uncle of an Ale House founder, met his demise in a bar fight in 1886 in Sheboygan Wisconsin. Louie’s Cup, the dented and scuffed trophy cup that is awarded to the first place boat is celebrated as the drinking vessel bashed over Uncle Louie’s head, leading to his ultimate demise. The truth is, the cup was repeatedly bashed into a parking meter outside the trophy store by regatta founders who wanted to further Louie’s legend.
Another colorful piece of the charity regatta is the sanctioned bribery called "Louie’s Challenge". Starting in 2001, boat crews could bribe the race committee for a better finish position, with all money going to Children’s Hospital.
In 2002 Internationally recognized Mount Gay Rum came on board as a sponsor and their distinctive red hats became part of the Milwaukee sailing attire. A new trophy is being awarded this year, adding to the lineup of polished cups and plaques, for the best costumed crew of the regatta. "The Cutlass" trophy was inspired in 2006 by the fun loving costumed "keg bears" and donated by Captain Tom (Bucket-O-Margaritas) Young.
Children’s Hospital of Wisconsin, founded in 1894, is one of the leading centers for pediatric health care in the United States. In a comprehensive survey, Child Magazine rated the private, independent, not-for-profit hospital as the third best children’s hospital in the nation.