Pewaukee Yacht Club hosts a number of regattas during each year's sailing season. Spaced throughout the year from spring through fall, these events attract competitors from all over the country and provide tremendous tests of skill as well as fantastic spectating. The club hosts the following permanent regattas every year:

• Class MC North Americans (May 3-4)
• Class X White Cap (May 10)
• Class A Spring Classic (May 10-11)
• Class C Over 40 (June 26-27)
• Class E Blue Chip (September 19-21)

The 2008 events bid for and won by Pewaukee Yacht Club are:

• Melges 17 ILYA Championship (July 19 - July 20)
• Class MC MCSA National Championship (July 24 - 26)