The Pleon Yacht Club was founded on June 29, 1887 by a group of boys with boats too small and finances too meager to join the older senior clubs in Marblehead. Their objective was to promote small boat sailing and to encourage sportsmanship. For a name they chose Pleon, which comes from the Greek meaning "sailing". The familiar red and blue burgee with the white star was designed at the time by Howard Whitcomb.

Without realizing the significance of their act, the first commodore, Arthur Goodwin Wood, and his fellow founders had laid the cornerstone of junior yachting in the United States. The Pleon Yacht Club can proudly claim the title, "oldest junior yacht club in the world".

The First Generations

The history of the Pleon can be divided into three eras. The exact limits of the first are somewhat in doubt. The club was very active from 1887 till 1892 at which point most of its members transferred their activities to the senior clubs. An informal organization of the old members continued to exist, however, until 1902. In 1905, a new generation of juniors formed the Ajax Yacht Club. They were soon persuaded by Commodore Wood to adopt the name Pleon, which had ceased to exist after 1902. During the second era, the club prospered under the guidance of Arthur Wood, Donald R. deLoriea, and Henry A. Knowles. Pleon activities gained considerable recognition from the senior clubs; the handicap classes gaining a place in the 1913 Mid-Summer Race Week, now known as Marblehead Race Week, and on the 1915 championship card. But the first World War caused a suspension of formal activities in 1917. There was informal racing, however, the new Brutal Beasts being a notable addition, and the spirit of the club was kept alive. In 1919, David Percival was elected Commodore by the remaining juniors and the third era was started. The next year Richard S. Thayer began his term as Commodore which was to last six years and bring the Pleon and junior yachting national fame.

The National Stage

1921, Commodore Thayer and his crew won the first Sears Cup series- the National Junior Sailing Championship for Pleon. This feat was repeated in 1924 by his brother Harry "Bob" Thayer. A few days later the entire club manned the yacht America from Boston to Marblehead on the first leg of her final voyage to Annapolis.

In 1927 when Commodore Wood died, Pleon was observing its 40th year under Commodore Laurence F. "David" Percival. The success and fame of the club continued in the ensuing years. Milestones were Stanton Deland's victory in the 1931 Prince of Wales Cup and the establishment of the Graduate Board to assist the club's officers. The Golden Anniversary was celebrated in 1937 during Peter Langmaid's term as Commodore.

Between The Wars

Much of the organizing efforts between wars was the work of Leonard M. Fowle, Jr., who served the club in many capacities, both as a junior yachtsman and later as chairman of the Graduate Committee. Many of 51 the permanent racing trophies and traditions date from this period. First came the Henry A. Knowles Memorial Trophy and a cruise in 1922. The Gold Medal of Merit and the Bang-and-Go-Back Race date from 1926. Pleon's highest honor, the Arthur Goodwin Memorial Bowl; the Snail Cup, commemorating the club's first flagship, and the initial Brutal Beast Tournament marked the anniversary year of 1927. The annual Race Week Junior Regatta and the Donald R. deLoreia Memorial Trophy, a small boat companion of the Knowles Trophy followed a later year.

Annual Honors

During the 1930's, list of annual Pleon honors grew dramatically. New additions included: the Venture Trophy for the girls' championship given by fleet captain Nancy Leiter, the Leonard Munn Fowle Memorial Medal for improvement, the William Leeds Carlton Memorial Trophy for the already established Brutal Beast Tournament, honoring an old friend of the club, the annual team race with Seawanhaka Corinthian Junior Yacht Club for the Phillip J. Roosevelt Trophy and the Margaret McKim Trophy for excellence in coastwise navigation.

The William Upham Swan Memorial Trophy made from the yacht America for recipients of the Sportsmanship Medal and the Frederick J. Shepard III Memorial Trophy commemorating a former commodore who gave his life in World War II were added in 1942 and 1944 respectively. After World War II, Pleon acquired the Corinthian Yacht Club Trophy for the Bang-and-Go-Back Race, and in 1951 the Pleon Trophy for outstanding administrative service to the club was set up by the Board of Directors and took its place beside the Shepard Trophy as one of Pleon's highest awards. The Mason Plaque was offered for Turnabout Competition and team race series with the Beverly Yacht Club of Marion for the Franklin Delano Roosevelt Bowl and with the Wadawanuck Yacht Club of Stonington, Connecticut were organized. And, in 1963 Commodore William Peaver donated the Peaver Bowl to be given to an outstanding member of the Regular Pleon Sailing Program.

Program Evolution

In 1939, with the cooperation of the Eastern Yacht Club, a nautical instruction program was set up for juniors by the Pleon. Eric Olsen, the first instructor, created a valuable program in seamanship, navigation, and racing instruction with achievement rating awards. Instructors such as Pete Putnam, Dick Kimball, Bill Owens, Roger Hearne, Dick Cook, John Van Dusen, Will Johnson, and Jim Nathenson followed.

In 1963, the program was revitalized through a reorganization move which put it under the exclusive control of the Pleon after the noble experiment of a four-club control had outlived its practicality. The initial year, marked by expanded facilities, was an immediate success. The program accomplished what it set out to do: to provide more individual instruction through the use of an instructor in each of the three Lightnings used, and to set up a challenging program for the Sears Cup. Today instruction is provided in 420s, Lasers, Optimist Dinghies, and Sonars. In the early 2000s, local high school teams began using the club as an off-season base for training and thus began Pleon's new shoulder season programs which now include race coaching for Optimists and 420s in both the spring and the fall.

Championship Legacy

This reputation has been built up over the years by many Pleon members. Names such as Bobby Coulson, George O'Day, Ted Hood, Frank Scully, Jud Smith, John Marvin, Jack Blodgett, Dave Curtis, Robbie Doyle, Jon Wales, Dick Kimball, and Dudley Shepard come to mind. The Sears Cup has returned to Pleon many times since the Thayer brothers' victories. In 1950 it was won by Stephen Smithwick, in 1961 by Steve Wales, and in 1964 and 1965 by Robert Doyle. Since 1964 Pleon has been represented by a number of excellent young sailors. Robbie Doyle later went on to represent the United States in the 1968 Olympics as an alternate and was an intercollegiate All-American. Rob was the 1970 O'Day champion. His brother, Richie, was an All-American at Notre Dame for three years. Richie, in 1970, and Rob Hallawell of the U.S. Navel Academy in 1987, were named College Sailor of the Year- the highest award in intercollegiate sailing. Tom Bernard was an All- American at the Coast Guard Academy. David Curtis, a former Tufts All- American, won the 1986 J/24 and Soling World Championships.

Peter Warren took the runner-up spot in the '67 Sears Cup, and in 1969, won the 110 District championship, the North Shore Men's title, and was the first Pleon representative ever to win the New England's Men's Championship. He finished second in the Mallory Cup.

In 1970, Steve Wales, Doug Jones, and Rich Wilson were third in the Mallory Cup, and Tom Hildreth, Steve Hill, and Rich Wilson were in the finals of the Prince of Wales Trophy. All are products of Pleon.

In 1970, 14-year-old Mark O'Connor won the 110 Districts and National Championships and Jud Smith and Carl Hoyt took the W.C. Wood Trophy for the Mass. Bay Midget Championships. Stuart Wales skippered and Bonnie Eissner crewed to win the Wood Trophy in 1985 and 1986. Pleon sailors Tyler and Ethan Doyle won the Trophy in 1990, Ethan Doyle and Jason Hood captured this MIT event in 1991, and Thomas Barrows and Liam Kraft recaptured the Wood in 2001. Pleon sailors Thomas Hornos and Alex Cook returned and were victorious in 2002.

In 1986, Pleon sailors swept all three junior Mass. Bay Championships. Charlie Flather, Jon Wales, and Andrew Macaulay won the triplehanded Gray Trophy. Hugh Hallawell and Buster Pike won the Doublehanded Charles Trophy. Alex Dufee won the Curtis Junior Singlehanded Trophy. The summer of 1987 brought Pleon's 100th year and as a celebration of this milestone, the yacht club hosted the U.S. Junior National Sailing Championships for the Sears, Bemis, and Smythe trophies. This event brought sailors from all over the country to Marblehead.

The following summer, Pleon was lucky enough to be able to co-host the U.S. Finn Class Olympic Trials with the neighboring Eastern Yacht Club. This event provided a chance to meet some of the top Olympic hopefuls, man the stake boats and mark boats, watch exciting action on the race course, and attend a racing clinic held by the competitors. 

1998 was a busy year at Pleon. Marblehead Junior Race Week became a separate regatta managed by Pleon volunteers. Pleon also hosted the Optimist National Championships. With over 300 sailors in attendance, it was the largest single one-design regatta in the history of North America. GIven the success of these events, the Massachusetts Bay Sailing Association voted Pleon "Yacht Club of the Year". In 2005, Pleon celebrated the 50th consecutive year of its involvement with Junior Race Week. That same year, Thomas Barrows won the US Youth Sailing Championship in the Laser Class and earned the right to compete for the O'Day Trophy.

In 2008, Pleon alum Thomas Barrows represented the Virgin Islands in the Olympics sailing lasers and competed again at the 2016 Olympics for the U.S. in the high-performance 49er.

International Flavor

During the last decade of the 20th century and into the next, Pleon added to its roster of coaches many from outside of the US. Instructors have come from Ireland, Denmark, England, Sweden and New Zealand. Pleon sailors, in turn, have had the chance to sail in other waters. In 2000 and 2001 sailors went to Toronto and Bermuda to participate in a friendship regatta with the Royal Canadian Yacht Club, the Royal Bermuda Yacht Club and the American Yacht Club. Pleon members also became part of the North American Station of the Royal Scandinavian Yacht Clubs and sailed in their 5 club youth regattas... Jessica Clayton and Jay Connolly in Finland in 2001, Jen Doyle and Seamus Kraft in Denmark in 2002 and Lindsay Rogers in Sweeden in 2003. Pleon was also fortunate in July of 2000 to have Russell Coutts, two-time America's Cup winner, come to speak with Pleon sailors as well as Pleon alumni and supporters.

Leadership & Traditions

Though learning to sail and refining one's racing skills is the primary focus of a Pleon member, he or she also enjoys other activities at the club. There are movie nights, golf and bowling nights, and "sail with or against your parents nights". Though it has not been done for a number of years, the Clambake was a popular social activity. Everyone looks forward to the year when they can attend the Commodore's Ball and dance under the stars. Whether you call it "Goody Wood Day" or "Great Pleon Yacht Club History continued 55 Day", this break from regular classes is a day to celebrate being together at Pleon. Pleon members, young and old, can recall the "Bang and Go Back" races, the watermelon races, Slip and Slide, mud wrestling, creatively constructing a boat out of cardboard, duct tape, trash bags and sailing it until it sinks, the egg toss and the cake decorating/eating events! A recent addition to these activities is the "Rockmore Cup" - a race for all Pleon members from the Pleon dock to the Rockmore, a floating restaurant, for lunch.

The Clubhouse

In 1950 Pleon realized a long-held dream to have its own clubhouse. In the twenties there were several weak attempts to set up clubhouses on Marblehead Neck, but they were unsuccessful. Early in the next decade the Eastern Yacht Club made their old junior room, located under the main dining room, available to the Pleon. It served its purpose as center for the activities of the club for more than ten years. The Golden Anniversary Banquet was held there. Although it was enlarged and remodeled in 1946, it still left something lacking.

Fire destroyed this house in 1947 and Pleon was again homeless, but the officers saw this as an opportunity to fulfill their dream. For the next three years funds were raised by Commodores Jack Blodgett, Brad Marvin, Joe Parker, and Vice Commodore P. Tapley Stephenson, who headed the building committee. Members of the Pleon worked hard, each contributing his share in making the dream a reality. Through dances, parties, and the generosity of parents and friends and previous funds, enough money was raised to build the present clubhouse on land leased from the Eastern. It was an achievement to be proud of, a sincere reflection of Pleon spirit. It showed how much the Pleon meant to its members. The clubhouse was officially dedicated in June 1950.

Pleon added to its facilities in 1957 with its own Race Committee Boat and in 1958 with a float of its own, which proved valuable for many uses, the sailing program being paramount. These improvements helped to make the Pleon an independent club. It no longer had to rely heavily on the generosity of the senior clubs. The acquiring of property required that the club be incorporated and therefore in 1949 the Senior Board of Directors was established to meet state laws. This board has proved helpful to the officers of the club and yet has kept its place as an advisory board, thus preserving the independence of this junior yacht club.

In the early 2000s, a new clubhouse was built on the site where the previous one had stood for decades near the Eastern Yacht Club crane pier. Resembling an airplane hanger with a distinctive arched shape and large garage doors that open to dramatically unify the club's main room and its exterior deck space, the new clubhouse provided a much-needed upgrade but held onto some of the bohemian atmosphere that distinguished the original.

The Beat Goes On

Pleon now boasts some 388 members and club membership continues to grow. More activities, both on and off the water, are organized by the officers and sailing instructors than ever before. There is a lot to live up to in Pleon and the past has shown that there is ample opportunity to do this. The traditions of Pleon guide its members into becoming worthy participants in the world of sailing, where sportsmanship, skill, and spirit rank highest.