The regatta was originally funded in 1959 by Mrs. Katherine Conroy, who contributed five thousand dollars and the Founder's Bowl to The Gunnery’s coach, Rod Beebe, so that he could organize the regatta for the first time. Three schools, Gunnery, Choate and Haverford, entered the event. The first regatta took place on the other side of the lake, the New Preston side, over a 3/4 mile course and was won by The Gunnery. The early years of the regatta were dominated by South Kent School and Buckingham Browne and Nichols. In fact, these runs of victories were not broken until 1976 when Salisbury fired down the course, beating all opposition to lift the Founder's day trophy. In 1978, girls' teams were introduced to the event with a race length of 1000m. In the same year the race was moved from the New Preston side of the lake to the State Park side. The Salisbury boys' team completed a trio of wins, proving the distance change from 3/4 mile to 1500m was no great adjustment for their team. At this point there were eight different schools competing in the regatta. During the 1980s, the regatta grew in size as more schools were introduced to the event. Institutions like Groton, Pomfret, and St. Marks all met with success at the regatta, lifting the boys' points trophy in different years.