Pequot Yacht Club was founded in 1920—not in a grand boathouse, but in Fred Bedford’s living room in Greens Farms. Bedford met with a few like-minded sailors who wanted a club focused not on prestige but on pure sailing. They set dues at $25 and launched a club with 33 members, a handful of boats, and one big idea: make Southport a hub for competitive sailing.
The timing was perfect. Just a few years earlier, Southport Harbor had been deepened as part of the construction of the Country Club of Fairfield. That made it newly suitable for the keelboats Bedford and friends envisioned. With the harbor improved and demand growing, the club leased its first building on the water—a modest setup that served as the clubhouse from 1921 to 1926.
But Southport sailing was already booming. Local regattas drew boats from Westport and Bridgeport. By 1926, Pequot purchased and converted a four-story warehouse which became the two-story clubhouse still in use today.
The club’s golden era with the Atlantic class began in 1928, when a prototype Atlantic handily beat a Star in a trial sail. Bedford made the switch immediately and brought 19 friends with him. Pequot hosted the first Atlantic Class Championship in 1929 and went on to dominate the class, with skippers like Briggs Cunningham—who would later win the America’s Cup—cutting their teeth in Southport waters.
Through the Great Depression and World War II, Pequot endured. The senior fleet thinned, but thanks to its strong junior program, the club kept thriving. By 1934, there were 116 junior sailors. In the 1940s, Pequot’s Atlantics won eight of ten national titles.
Over time, the fleet evolved. Auxiliaries and cruising boats gained popularity in the ’50s and ’60s, while one-design sailing saw a renaissance in the ’80s and ’90s with Thistles and Ideal 18s. The club stayed true to its roots—competitive, low-key, and member-run.
Perhaps most notable today is Pequot’s quiet push for access. Programs like Sailing with Neighbors, launched with Family Services Woodfield, brought sailing to youth who’d never even seen a harbor. The club also opened programs to non-members, including Frostbite winter sailing, a robust junior sailing program, and partnerships with local high schools.
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