In 1954 a handful of Penguins converged on a small lake in north Nashville to compete in the first Tennessean Regatta sponsored jointly by the Nashville Sailing Association and Nashville's morning newspaper, The Tennessean. The winner of that regatta won the first challenge trophy established by the publisher of The Tennessean, the late Silliman Evans, Jr., a yachting enthusiast. After holding the regatta on Kentucky Lake for a short time, HIYC brought it home to Old Hickory Lake where it cranks up each year in early spring under the chairmanship of the Vice Commodore.

This regatta was run for the last time in 2013, after dwindling coverage from its namesake newspaper.  A new Spring regatta was founded, the OL Shultz Hospice Regatta.