Racing on Great South Bay emerged in the late 1880s when wealthy Brooklyn and New York yachtsman who summered in the area raced against local, year-round resident, trade sailors, who often acted as paid skippers. They raced shallow-draft boats, built either by professional or amateur builders, in separate classes rated by length. These early classes, the larger, sloop-rigged P, Q and R classes, and the smaller V, W, and X catboats suited the shoal water of Great South Bay. The yachtsman formed yacht clubs as a base for sailing activity to promote sociability and recreation among members and to encourage proficiency in members handling their yachts. Membership was originally limited to men, and at each club some strong personalities desiring the fastest boat for racing emerged and strong social ties were formed. These early racing sailors recognized the necessity to link individuals and their clubs together.

On September 27, 1906, J. Adolf Mollenhauer, Commodore of Penataquit Corinthian Yacht Club in Bay Shore held a meeting at his club to found the Great South Bay Yacht Racing Association. Attendees William Candee of Penataquit, Alexander N. Cook of Bellport Bay Yacht Club, Francis Williams and Edward Bleecker of Unqua Corinthian Yacht Club, Charles Searle and Joseph W. Lawrence of Babylon Yacht Club, and Joseph Wood and Dr. George E. Rice of South Side Yacht Club in Sayville united to promote more organized racing. Mollenhauer was elected President and Lawrence was elected Secretary and Treasurer. Delegates who represented each Member Club and the Officers and Chairmen of Committees ran the organization. The founders wrote a Constitution and By-Laws to establish the authority and rules to operate, and organized a multitude of racing opportunities. Soon the original member clubs were joined by South Shore Yacht Club in Patchogue.

Many traditions began. Member clubs and the Association provided elaborate, silver prizes for these races and engraved the name of the winning yacht beneath the name of the trophy, date and place. For the first annual Cruise Week in 1907, the Association published a Registry of Yachts, and established and published handicaps in a 6 by 9 inch pamphlet, which eventually become a small book published yearly. Another early tradition, to retire a trophy after the same person won it three times, began and this resulted in most early perpetual trophies not being in the possession of the Association. The Association also began to include more clubs.

The Association established many perpetual prizes and traditions during the decade beginning with 1920. A Special Prize in 1920 for Cruise Week, now called Race Week, was awarded to the yacht making the fastest time over the course at Sayville. It was won by Constance a P Class yacht. Subsequent winners were: 1921 Eagle, 1922 Dixie, 1923 Bee, 1924 Invader, 1925 Avis, 1926 Eskawaja, 1927 Constance, 1928 Avis, 1929 and 1930 Edna, 1931 Windward II, 1932 to 1935 Constance and Duncan Arnold. And, the Association grew when the Yacht Squadron of Westhampton left the Yacht Racing Association of Southeastern Long Island to join GSBYRA in 1922. The first advertisement appeared on the back cover of the Association year book to help defray the publishing cost in 1927, and the Association awarded a gold, perpetual Fire Island Cup, to a registered yacht receiving the greatest number of points in her class in Race Week, provided 4 boats started and finished in class in 5 scheduled races. First won by Montauk year future recorded winners were: 1928 and 1929 TorrupII, 1930 and 1931 to Buddy Smith in an M class sloop. The Gil Smith Perpetual Trophy was given by owners of P Class boats for the P boat with largest number of points during invitations and cruise week. Recorded winners included 1929 and 1930 Edna, and 1931 Constance. The Brown’s River Trophy was given by Sayville to the yacht with the best performance during Cruise Week by selecting only the score from the yacht’s single best race. The Commodore George A. Corry Trophy (father and organizer of Star Class) was established for the Star class in 1929. Recorded winners were: 1929 Budsal II Frank Robinson, 1930 and 1931 Wings C. & J. Pflug, 1932, 1933, 1934, 1935 H. Meislan and L. R. Bowdan, Jr., and 1936 to 1940 Draco II, skippered by Edward V. Ketcham, Jr.

By the 25th anniversary of the Association in 1931, twelve member clubs extended from Freeport to Quogue. Under the leadership of President Edward V. Ketcham, the 1931 member clubs included Babylon Yacht Club (1906), Bay Shore Yacht Club (1906), Bellport Bay Yacht Club (1906), Cedarhurst Yacht Club, Fire Island Yacht Club (1927), Point O’ Woods Yacht Club, Sayville Yacht Club, Shinnecock Yacht Club (1930), South Shore Yacht Club (1907), Timber Point Yacht Club (1926), Unqua Corinthian Yacht Club (1906), and Yacht Squadron of Westhampton (1922). The Association as a member of the North American Yacht Racing Union published the rules of racing in the yearbook. When NAYRU established junior triple-handed and women’s championship competitions, the Association formed the Gulden and Morgan competitions. Commodore Frank Gulden donated a silver relief plaque made by Tiffany for the junior championship and Henry Morgan donated a silver bowl for the women’s championship. A new tradition began as these trophies were engraved with the names of winner and medals were given to the winners to keep instead of the trophy. Commodore William H. Picken donated a midget championship trophy for children younger than juniors, and the Association donated the Great South Bay Bowl for an eight Association Middle Atlantic Championship.

As the numbers of boats racing increased to larger numbers within classes, other innovations came into existence. The 1936 Association year book listed class captain orders for Race Week etiquette, more advertising, and paragraphs of tips “From the Crows Nest” by Skippers Mate. Divisions were made within classes and skippers needed to check the yacht club bulletin boards daily for section assignments to a division. In the Star Class, when 20 or more Stars raced, 2 sections were made. First division boats were required to carry a white 4 by 12 inch streamer on their boom. The Association established the Harry Growtage Memorial Cup for the fastest corrected time over a designated course to be sailed in a Labor Day Regatta in 1939 to replace the retired Queen of the Bay Cup. Requirements included that the race be held under the auspices of a GSBYRA Member Club, confined to restricted classes, and only boats having entered and completed a race in at least 4 Invitation regattas during the season were eligible. It was awarded to Querida, an R Class boat from Babylon. The Association followed the lead of NAYRU and in 1952 established a men’s championship for the Fenner Bowl.

By the 50th anniversary of the Association, fourteen member clubs comprised the roster under President E. Carleton Arink. In 1956 the member clubs included Babylon Yacht Club, Bayberry Yacht Club, Bay Shore Yacht Club, Bellport Bay Yacht Club, Cedarhurst Yacht Club, Domino Yacht Club, Moriches Yacht Club, Narrasketuck Yacht Club, Point O’ Woods Yacht Squadron, Quantuck Yacht Club, Sayville Yacht Club, Shinnecock Yacht Club, South Bay Cruising Club, and Westhampton Yacht Squadron.

In an innovative move in 1964, the Association purchased 8 Mobjack class boats for triple-handed championship competition. It was one of the few Associations to own boats. With a high number of competitors, the Association often divided competition into an east and west sub division before a run off competition. The Association Mobjack fleet had many storage areas during their life span: the marshy area now the Maritime Museum, later the Snapper Inn, Moriches Yacht Club, and in 1973 the Long Island Yacht Club. During the sixties, the Association established the Westin and Shinnecock Championships in response to NAYRU establishing single-handed competitions for adults and juniors. When NAYRU changed its name in 1975 to the United States Yacht Racing Union, the Association became a member of USYRU. By 1978, the Association embarked on a three year fund raising initiative to purchase 6 new Mobjacks to replace the aging original fleet. And, once again the Association grew with Magoun Landing, a local property owners group, becoming a member in 1980.

By the 75th anniversary of the Association, seventeen member clubs comprised the roster under President William B. Ludlum. In 1981 the member clubs included Babylon Yacht Club, Bayberry Yacht Club, Bay Shore Yacht Club, Bellport Bay Yacht Club, Cedarhurst Yacht Club, Hempstead Bay Yacht Club, Long Island Yacht Club, Magoun Landing Yacht Club, Moriches Yacht Club, Narrasketuck Yacht Club, Point O’ Woods Yacht Squadron, Saltaire Yacht Club, Sayville Yacht Club, South Bay Cruising Club, Unqua Corinthian Yacht Club, Westhampton Yacht Squadron, and Wet Pants Sailing Association. Finally the Association purchased new Mobjacks in 1981 with donations received from nearly three dozen individuals and ten clubs: Babylon, Bayberry, Bay Shore, Bellport Bay, Hempstead Bay, Moriches, Narrasketuck, Sayville, Wet Pants and Westhampton.

As USYRU added more championships, the Association established the Furman match race Championship and the Patin double-handed junior Patin Championship and made more bold moves. Membership in the Association rose to eighteen clubs in 1982 when Hobie Fleet 124 joined. The Association added a $10 sustaining membership category. Another innovation by President Glenn Schmidt established a Scholarship Fund and the Association awarded sailing grants to three recipients in 1988 from contributions to the fund. USYRU evolved into US SAILING in 1991 and Bay Shore Yacht Club became the home for the Association owned Mobjacks in 1992. As one of the eight members of a Midget Championship Association, the Association established the single-handed Orr Championship in 1993. Eight Association clubs also sponsored Friday junior regattas in 1993. For 1997 the Optimist replaced the Sunfish in the Association midget championship. Both Hobie Fleet 124 and Magoun Landing disbanded and left the Association in 2002, twenty years after joining. The Association developed a website in 2004 to aid communication. And finally the Club 420 replaced the Mobjack for the Picken midget championship in 2005.

For the 100th Anniversary sixteen clubs remained members of the Association headed by President John Everitt. The Association designated its website as the official voice and amended the By-Laws to create new membership categories that included more types of sailing organizations. And President Everitt encouraged the after race party tradition be revived at Race Week and Invitational Regattas. The Association encouraged replacing the aging Mobjack championship fleet with another class boat narrowing the selection to the Flying Scot and encouraged Member Clubs to purchase a club-owned Flying Scot that could be used for the triple-handed championships and for adult sailing lessons. After raising funds, the Association purchased two factory refurbished Flying Scots for charter and twelve identical suits of sails for competition in 2007.  Glenn Schmidt and President Gerard Holwell drove to Maryland to transport the boats north to Bay Shore Yacht Club. Glenn found buyers for the six Mobjacks. Russell and Lenny Pearson handled the Flying Scots for charter in the triple-handed championships, assigned sails from the inventory to all competitors, and inspected returned boats and sail inventory after each event. All triple-handed championship competitors were now required to sail either a club owned or chartered GSBYRA Flying Scot with Association owned sails used only for those events. Additionally all bay championships used sailing instructions generated according to GSBYRA outlines. Next the Association purchased an enclosed trailer that Jerry Holwell outfitted with shelves for the storage of the sail inventory, and Jerry arranged for the trailer to reside at Bay Shore Yacht Club. Triple-handed championships could now be held at any club, not just at Bay Shore as had been the practice.

Several organizations expressed interest in joining the Association during 2009. The Association’s first female President, MaryAnn Deering, appointed a committee to investigate the organizations and provide recommendations. Seaview Sailing Yacht Club became a Provisionary Member in 2009. Shinnecock Yacht Club returned as a Full Member Club and South Bay Watersports Association became a Full Member of GBSYRA in 2010.

The ebb and flow of similarities and constant change created over one hundred years of historic and exalted competition on Great South Bay. Competition flooded the bay with enough boats to promote the development of one design rules for building yachts. Management of class competition surged within and among member clubs. Races run at various clubs led to an organized schedule to be agreed upon. Dominant personalities emerged and camaraderie swelled as members traveled and bonded at single day to week long, week end and multiple day events. Uniforms distinguished Committees and Officers from competitors. Innovative design and different boat building materials spawned the change from gaff rig to Marconi rig, from cotton sail to Dacron sail, from wood hull to fiberglass hull, from wood spar, rudder, centerboard, and tiller to aluminum spar, rudder, centerboard and tiller, from displacement hull to planning hull, from single-hull to multiple-hull, and eventually to include carbon fiber everywhere. A few changes overwhelmed and submerged some clubs and classes into extinction. And finally, a lofty change emerged from the coalition of clubs and strong personalities to recognize female participation and leadership within the clubs that spilled over into the Association. Changes are inevitable, yet the love of sailing and competition never cease.

Several excerpts from A History of Westhampton Yacht Squadron 1890-1965 by Standish Medina quote Mrs. McClintock remembering her youth. “Just as sailing was the basis of that life, so racing was the thrill of it: All talk was of sail area, overall length, time allowance, every phase of racing receiving the keenest attention. For that was no idle, light minded sport, and each youthful captain was out to win - in fact, was sure he would win”. “The boat built, next in importance was the selection of crew, and no skipper worthy of the name chose his crew for friendship’s sake alone but scoured about for bluff and heavy tars who were light on their feet, strong in their arms and (with 3-reef gales in mind) a bit on the plump side. The crew secured, there began practice; in fair weather and in foul, in blistering calm and in drenching gale, all to get them attuned to the idiosyncrasies of the boat, to know when, in a calm, to lie flat and light in the cockpit, scarcely breathing, and when, in a gale, to throw themselves, heavy and tense on their luckless stomachs, far over the side and let the waves wash where they would.” The lore of racing sailboats continues unchanged.