The Twenty Footer class, as it was then called, had no rules – other than the boat had to be twenty feet. in 1938 at the Annapolis yacht Club, Ozzie Owings held an organizational meeting to form the Chesapeake 20 class with dues at $2 each. He said the purpose of the association was to prevent being overrun by “freaks and racing machines such as Double Trouble, the Owens scow.” While the sail area and length werefixed, Chesapeake 20 rules remain only about three pages long and as described by Billy Heinz in a 1942 Yachting Magazine article, remained an “evolution” class.

in 1939, Cap’n dick was approached by Andrew Kramer, President of Annapolis Bank and Trust, who told him “to get serious about building Chesapeake 20s.” Kramer provided a loan to build twenty Chesapeake 20s which were “mass produced” in lots of four at $600 each. The first of these boats was Stormy, now registered with the Maryland Inventory of Historic Properties. in 1942, the “Hartge 20” was advertized as a “racing sloop or day sailor”: “(by leaning the boat over on a beach) no haul out necessary to keep the bottom clean”... “get a Twenty, the smartest boat you will ever sail”... “Here it comes: Twenty feet of able, fast racing sloop.”...”(With wide decks,) the buoyancy of the Hartge Twenty is such that she will not fill with water, even with the masthead awash.” Cap’n dick Hartge built about 40 round-bottom Chesapeake 20s from 1939 until 1943, and only four after World War ii as cedar wood and materials were in short supply and expensive. He said that “i lost my shirt” after the war when the cost to build them doubled.

Regattas were held throughout the middle Bay and on the Potomac in Washington, d.C. prior to World War II. Racing continued through the war years and results were reported to the troops in the field in weekly Galesville Home News. Usually, Chesapeake 20s were either sailed or towed by water to away regattas, as they continue to be today.