Pequot Yacht Club came to be through the efforts of Fred Bedford, in addition to Harold Lloyd, Johannes Schiott and Lawrence Craufurd. The first meeting of Pequot Yacht Club was held in the Greens Farms home of Fred Bedford on October 25, 1920. These Founding Fathers, in addition to a group of five or six interested sailors, agreed to form a yacht club for the purpose of reviving and promoting competitive sailing. In November 1920, a constitution and by-laws were drafted and ratified. Subsequently, the Club, consisting of 33 members, elected officers and set annual dues at $25.00 Although the initial meeting took place in Greens Farms, Connecticut, the history of the Pequot Yacht Club is unquestionably rooted in the history of nearby Southport Harbor which had been deepened in 1916 during construction of a golf course.

The Club’s first officers were authorized in November 1920 to negotiate the lease for the a building on the water in Southport, which was the PYC’s clubhouse from 1921 to 1926.

In April 1921, at the Club’s next recorded meeting, the character of the Club’s early years was established. The racing calendar was the primary issue. The Club’s first racing fleet consisted of four “R” boats (35 ft. sloops), five “K” boats, and one Star. Over the years, the Club has remained as much as its founders envisioned: an organization devoted simply to sailing.

As early as 1923, Club members believed that an active junior program was the key to sailing’s future. In 1923, the Club sponsored the first junior regatta for crews under 18 in the Yacht Racing Association of Long Island Sound. The first formal junior program at the Club was started the following summer.

By 1925 the original clubhouse was becoming overcrowded, and by September 1926, a four-story warehouse building had been converted into the two-story clubhouse used by the Club to this day.

The Atlantic class came to the Club in the fall of 1928 when a demonstration boat handily beat its Star competition. Twenty Atlantics were ordered immediately. In 1929 the Club ran the first Atlantic Class championship.

The Great Depression had a negative impact on the Club’s financial health and Senior membership dropped significantly. However, prior investment in a strong junior program was vindicated: by 1934 there were 116 junior members.

Although the Second World War made yachting a matter of secondary importance in Southport, the Club’s Atlantics continued the tradition of vigorous participation in class racing. By 1949, Atlantic sailors from Pequot had won the national championships for eight of the decade’s years.