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 2-3)
• Class X White Cap (May 9)
• Laser Spring Regatta (May 9)
• Class C Over 40 (June 25-26)
• Class E Blue Chip (September 25-27)

The 2009 events bid for and won by Pewaukee Yacht Club are:

• Class C National Championship (June 19-21)
• Class E ILYA Invitational (July 10-12)