Louie’s Last Regatta was started in 1999 by a group of Milwaukee sailors who basically wanted one more sailing regatta before they had to pull their boats from the water. To make their effort more attractive to sailors thinking about snow shovels and ski trips this devoted group decided to make Louie’s into a charity event. The first Louie’s Last Regatta brought in $900 and twelve boats participated.

The event grew steadily in popularity and money raised. Major sponsors came forward, boat crews donated and the post race party grew. Louie’s Challenge otherwise known as “sanctioned bribery” was a unique and surprisingly popular fund raising feature of the Regatta. Started in 2001 boat crews could bribe the race committee for a better finish position, with all money going to Children’s Hospital. The silent action was introduced in 2001. 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. In 2004 SAILING MAGAZINE listed Louie’s Last Regatta as one of the Top Ten Best Sailing events in the country.

In 2005 Louie’s 7th Last Regatta had over 100 boats entered and raised over $80,000 for Children’s Hospital of Wisconsin. Louie’s is now one of the top participation regattas in the Great Lakes and one of the largest fund raising regattas in the nation.

In 2006 the Lake Michigan sailing community got together and raised over $123,000.00 for the Children’s Hospital of Milwaukee. For that you should all be proud. With 131 registered boats and over 450 sailors and crew, Louie’s Regatta continues to grow and provide for CHW.

In 2007 the weather was great, the participant generous and the staff and children at Children’s Hospital of Wisconsin very thankful, Louie’s broke yet another record for generosity, raising over $131,000 with 145 boats registered.

In 2008 we had another great year, every one was generous, and we even made The Milwaukee Journal-Sentinel. This was the first year for the Sunday M.A.S.S. (Morning After Sail of Shame) Event, the annual race back to Waukegan, IL for Chicago-area boats.

Louie’s 12th Last Regatta of 2010 saw some changes. The regatta introduced two sections Solomon Juneau Section and the Flaming Damsel Section (once and twice around the famous beer can course respectively). This allowed for two sections of winners and also allowed more to finish the race and get to the party with their heads held high. It was also stirring sight to see Merlin, one of sailing’s most iconic boats, and Defiance, a 66 footer, duel it out at the front of the pack. The Launch Party was introduced this year to get the fundraising going early for Children’s Hospital of Wisconsin. Plus another winning idea sponsored by North Sails was introduced the “North Sails Ugliest Spinnaker Award.”

Lucky 13th was not so lucky since the sailing portion of the regatta was cancelled due to huge waterspouts right off the coast of Milwaukee. The party many be considered the finest ever had in yachting history, which included a footrace plus card draw to decide the event winners and prizes. It was in the rules — can you believe it?!

In 2013 Louie’s Last broke the $1,000,000 bench mark for total dollars raised for Children’s Hospital of Wisconsin. Along with beautiful weather, fine crew work and crew generosity this was a halmark year for the regatta. Thank you to all that made this possible!

This special event gained its name from the Milwaukee Ale House’s flagship brand “Louie’s Demise” Amber Ale. True Story…Louie Eishold, great uncle of an Ale House founder met his demise in a bar fight in 1886 in Sheboygan Wisconsin.

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