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The first era of sailboat racing consisted of contests between the fishermen’s skiffs. Later, summer residents joined in. In 1890 a group founded the Westhampton Country Club to socialize, play tennis and croquet and further sailboat racing. A small wooden building was put up at Moniebogue Bay where a dock was maintained.

In 1922, a yacht club was constructed at the foot of Speonk Shore Road. It was destroyed by the 1938 Hurricane. The depression and the hurricane forced the almost bankrupt Country Club to let the Yacht Club property be sold. On June 27, 1939 the Westhampton Yacht Squadron was renamed and land was purchased for $1,000 west of the old site. A small clubhouse was erected for $3,750. Racing continued until curtailed during WW ll. In 1955 two more pieces of property were bought for $2,500.

The now famous Fall Series was started in 1964 and became a part of the Squadron’s agenda. The Squadron’s 75th Anniversary was celebrated in 1965. In 1969 the present club house arrived by barge. It had been known as the Cedar Beach Club. The old club house became the Junior Yacht Club.

The Y Flyer Class started in 1970 with 12 boats crossing the line. The new trophy case was also installed that year. Our swimming pool was built in 1972 and in 1976 we had our first swim team. While tennis buffs played on our new all-weather court, the first wind surfer regatta was held. In 1977, the Squadron hosted the Area B semi-finals for the Women’s Nationals. Our team, having won the Morgan Bowl, placed 3rd.

The Eighties saw the Hampton Classic, an all-day Hobie Cat regatta and another wind surfer regatta. The first annual Past Commodores Dinner was held in 1985 honoring all past officers and directors

In 1990 the Squadron celebrated its centennial year with numerous sailing and social events. A GSBYRA invitational was held as well as the Flying Scot Regionals. A gala dinner dance was held with over 200 people attending.

The WYS Board of 1999 voted to put heat in the club house, thus allowing the club to remain open all year. A formal New Year’s Eve party was held to welcome the new millennium.

The SS Centennial Celebration was held on July 4, 2008. A committee of fifty people joined together to organized the parade, the races, the award’s dinner and the production of a centennial brochure. Forty six boats raced and over 200 came for dinner. The SS 76 was donated as the raffle prize by Rick Clifton and “The Magic Boat” was written by Meredith Medina; all in honor of our wonderful SS boats.

In 2008, WYS hosted the United States Optimist Dinghy Association (USODA) National Team Racing Championships attended by 20 teams, comprised of 90 competitors from Bermuda, Canada and many states from Maine to Texas.

In 2009, WYS hosted the US Sailing Junior Women’s Championship (Leiter Cup) raced in Lasers by 49 competitors from across the country.

In the spring of 2010 the Board approved the installation of an electric solar system. Ninety six photoelectric panels were installed on the roofs of the south side of the building thus reducing the cost of our overhead.

The GSBYRA’s 2010 Race Week was hosted by WYS on July 30th, 31st and August 1st, 2010. The weather was favorable and 10 races were held on the main course. There were 86 entrants in 13 different classes of sail boats. The competitors ranged in ages from 7 to senior citizens, with over fifty volunteers participating.