The school traces its roots to 1960, when Longshore Club Park first opened. Westport's Recreation Commission sponsored a public summer boating safety course for children, called Basic Boating. With no funding, a few borrowed rowboats, and volunteer instructors, students learned about safety and seamanship while rowing in the Saugatuck River entrance. The program was based in what is now known as the Rev. E.R. Strait Marina.

In 1962, the Recreation Commission obtained new plywood skiffs to replace the borrowed boats, and one year later, Westport acquired a fleet of 8' fiberglass sailing dinghies for public sailing instruction. This step made Westport one of the country's earliest pioneers in public access sailing programming.

In 1963, the American Fiberglass Corp. of Norwalk, makers of the 12' Aqua-Cat catamarans, loaned a fleet of their boats to the Town to provide advanced instruction and boat rentals. Longshore was the first pubic access program in the country to incorporate multihulls into its curriculum. By 1969, the Basic and Advanced programs merged and moved to pool cabanas where the school is located today. As enrollment swelled to over 400 students per summer, LSS quietly became the country's largest public sailing program of its kind, a distinction it has never surrendered.

Despite its popularity, the program nearly collapsed in the recession of the mid-70's. With Westport's recreation budget slashed and its well-used boats falling into disrepair; lack of funding brought the program to the brink of extinction. To save it, in 1975 the town out-sourced the school to John Kantor, a 10-year veteran supervising the program. He gave it the name Longshore Sailing School. Longshore has flourished ever since, outgrowing four buildings, leading to its current, two-story boathouse built in 2001.

Today, Longshore teaches approximately 2000 students a year on its fleet of over 100 sailboats and kayaks.