Presented in 1997 by the Cruising Division as a perpetual trophy to be awarded annually to the Fishing Bay Yacht Club member for support of the Cruising Division and for cruising the Chesapeake Bay with a sense of adventure in comradeship with fellow sailors.

The perpetual trophy is a ship's wheel with the name and purpose engraved on a center plate. Each year, a small plate engraved with the annual recipient's name and the year of the award will be placed around the wheel's outer edge. The recipient will also receive an engraved pewter cup to retain permanently.

The Trophy Committee is encouraged to consult with the Cruising Division Commander and Lt. Commander in reaching its decision.

The Board of Trustees may change the provisions of the award, if at any future date it becomes expedient to do so.

1997		Wayland W. Rennie
1998		Charles R. Jones
1999		Jamie Stalnaker
2000		Victor G. DeNunzio
2001		Allen M. & Alta Bower
2002		Gordon & Sheila Nelson
2003		Samuel M. & Nancy Stoakley
2004		Fay & John Koedel, Jr.
2005		Victor G. & Jane DeNunzio
2006		Anthony D. Sakowski Jr.
2007		Henry J. & Carolyn Schott
2008		Samuel M. & Nancy Stoakley
2009		John G. Koedel Jr.
2010		John G. Koedel Jr.
2011		Henry J. & Carolyn Schott
2012		Gordon B. Jr. & Jane Cutler
2013		Samuel L. Stoakley, Jr.
2014		George and Francis Sadler
2015		William & Lydia Strickland
2016		Anthony D. Sakowski, Jr.
2017		William T. Bennet
2018		Helen & Dacre Walker
2019		George and Lyons Burke
2020		Nancy Glinn Powell
2021		Parker and Kim Garrett
2022		John Koedel III
2023		Stuart Gregory