Cap'n Dick scaled down the Sea Witch II and Fred Davis built Mischief. In the first races, there were a few Comets, a Sneak Box, Ed Leatherbury's bateaux and others. Several sailors from Fairhaven also had Sixteens and came up to race. Dick also built a 16 for Jack Hazzard.
Next come a scaled down copy of the round bottom 20. The first one was a scaled version of Sea Witch named Mischief and bulit by Fred Davis. Aloha was built by Laurence Hartge with the help of Fred Davis. Paul Kirchner, a worker at the Hartge Yacht Yard, build Dolly and she was bought by Elsie Hartge and her husband, Hugh Wallis. Hugh Wallis also owned Shark in the 1930s. These boats raced at the same places and traveled to the same regattas as Chesapeake 20s. Some of the early names were Dot (J. Hazzard), Sue (A. Dixon), Buzzard # 181 (A. Feifer), Swan (C. Dixon), Flying Cloud, Aloha (Laurence Hartge), Miss X (Paul Kirschner), Adios, Rascal, and Shark.
The Chesapeake 16 organization was formed in 1938 and led by Lawrence Hartge. The class was sanction by the CBYRA and awarded Highpoint Trophies from 1948 to 1958. Two of the most consistent winners of the class where Hugh Wallis and J.E. Vieth.
Several Chesapeake 16s were also located at the Washington Sailing Marina in the late 1940s; and the last dwindling fleet at Bell Haven.
See race results of Chesapeake 16s at President's Cup ca 1937. Winner was Dot (Jack Hazard), No-Name (Arthur Fifer), Sue (A. Dixon), and Swan (C. Dixon)
