The 100th anniversary of Cape Cod’s classic Wianno Seniors will be celebrated this summer showcasing classic—and particularly American—Nantucket Sound memories.

Photo Courtesy of John Fallon

For the last 100 years, a small sloop designed and built on Cape Cod has been a vessel for much more than carefree summer sailing. The first Wianno Senior took its maiden voyage in 1914. The boat was commissioned by about a dozen local families and designed and built at Osterville’s historic boatyard, Crosby Yacht. The winds of fate helped this elegant, yet seaworthy sloop with spare clean lines and a sweeping expanse of sails, become an icon for Cape Cod sailors. Some—and certainly those who have sailed them—say the boats have shaped the course of American history along the way.

There are many stories to tell about this unpretentious, 25-foot ‘knockabout’, as recreational sailboats were called in the early days of Cape Cod’s resort towns. Designed by inspired boat designer and superb engineer, H. Manley Crosby, the Wianno Senior was created to handle the climatic changeability and unique geography of Nantucket Sound.

E.M. Crosby Boatworks in West Barnstable and Osterville’s original Crosby Yacht Yard are still building this sailing thoroughbred, although today’s boats cost a bit more than the 1914 price of $650 per boat. Just as it was in 1914, though, the Wianno Senior is being built today at 25 feet in length, 17-1/2 feet at the waterline, with a draft of 2-1/2 feet when the boat’s centerboard is up, making it the perfect boat for the shallow sandbox that is Nantucket Sound.

Seniors continue to carry the boat’s original gaff rig (a modified triangular main sail design that is a steadying factor for often gusty sailing such as that found in the Nantucket Sound) and the design’s imposing 366 square feet of sail. In 1986, Crosby Yacht launched the first fiberglass Senior. The new boats were carefully designed and built to match the original 1914 specifications, a necessity for those who still participate in one-design Wianno Senior races held week in and week out by Cape Cod and Martha’s Vineyard yacht clubs from June to September.

Wianno Seniors are so cherished by some that the boats are passed down in families like treasured sets of sterling silver, or rare works of art. In fact, the boats are often referred to by their hull numbers, rather than their names, emblematic of the fact that Seniors may change hands and even be given different names by successive owners—but each boat retains its own integrity and identity forever.

Hyannis Yacht Club’s Brad Tracy skippers Dauntless in a 2011 Scudder Cup race.

Every current or former Wianno Senior owner that we contacted was eager to share their own stories and photographs of #76 say, or #214. (In total, only 224 Wianno Seniors have been built, including the fiberglass models.) Current and past skippers talk about their fathers, grandmothers, brothers, aunts, and great great grandfathers and how these boats are keepers of cherished memories passed down from one generation to the next.

The owner of #172 Dixie is West Barnstable’s Lucy Steere, whose famous sailing family has been racing Seniors in Cape waters since 1927, and who remembers meeting H. Manley Crosby as a little girl. Over the years, Steere has given the design’s continued popularity a lot of thought. “I think a huge component of the Seniors’ appeal is that yes, these boats are beautiful and timeless, but there are a lot of boats out there like that,” says Steere, who notes that Dixie was one of the last wooden Seniors built by the Crosby Yacht Yard. “I think the main thing is that the Seniors have tied all these yacht clubs, people, and memories together, from Harwichport to Osterville and out to the Vineyard.”

Steere notes that the Senior is also the only boat that is a centerpiece of three Cape Cod museums: the Osterville Historical Society (where her Uncle David’s boat, Venture , is on display), John F. Kennedy Hyannis and the Cape Cod Maritime museums.

Steere’s devotion to her Senior, which is cared for each season by Ned Crosby of West Barnstable’s EM Crosby Boatworks, a descendant of the original boat builders who is still building the sloops today, is mirrored by that of Tim O’Keeffe of West Hyannisport, who sailed two Seniors, a wooden and a fiberglass model, both named Rapparee , with his brother Peter for more than 45 years.

O’Keeffe says the Seniors have retained their hold on Cape Cod sailors for a century because, though the boats are challenging to race, they can also be the perfect boat for relaxed cruising with friends on long summer days. “I always thought of the Senior as more than a racing boat. I really think the most fun I ever had was sailing Rapparee (#127) back from the Edgartown Regatta in the early 1980s,” says O’Keeffe.

Several original Seniors, included #5 Commy, which was owned by Frank Hagerman of Kansas, Missouri, whose daughter Abby was a famous female skipper. Also shown are portside, James Gaff Hinkle’s Fantasy, and #6 Snookums skippered by Wilton Crosby. Photos Courtesy Osterville Historical Society

“It was a 20-mile, downwind sail, and we were just going with it. We had invited some non-sailing friends, and we filled the boat until it couldn’t hold anymore and made the four-hour sail home to Hyannisport. We reached home and didn’t want to stop, so we sailed right up to Baxter’s Boathouse (in Hyannis Harbor), tied up there and kept the afternoon going for a few more hours. That was pretty hard to beat.”

Lucy Steere—whose father, Bruce, and uncle, David, were famous Senior racers from Harwichport’s Stone Horse Yacht Club—agrees, but notes that the Seniors can be a lot to handle when the wind is blowing hard across shallow Nantucket Sound.

“You can be out there on a bluebird day, when she’s going along smoothly in the water and everyone is comfortable, or you can be out there when it’s blowing 20-25 knots and that boat is sure going to challenge you,” says Steere.

Tim Fulham, chairman of the Wianno Senior Class Association and a lifelong sailor, says that despite the Seniors’ beauty and historic charm, the boats can throw different challenges at their skippers depending on the day, the weather— and the particular boat.

“The Seniors are remarkable seagoing boats and very well suited for the waters of Cape Cod,” says Fulham, “and the challenge of racing a Senior never goes away. But that kind of challenge is always an engaging part of a passion for things. Racing on a Senior is different every time.”

The Wianno Senior Class Association was created to connect the different fleets that grew up in the last century around yacht clubs in Osterville, Bass River, Harwichport, Hyannis and Hyannisport, and Edgartown. The association is planning a full schedule of activities this summer in celebration of the fleet’s 100^th year. Fulham says a recent book, commissioned by the association, shares details of the boat’s long history and relates stories of the people who sailed her.

The Wianno Senior Story: A Century on Nantucket Sound was written by a Marblehead sailor, Stan Grayson, who also completed several other books and reports on sailing for WoodenBoat magazine. “The most gratifying thing for me is that I had a creative vision to do a narrative that celebrates the Wianno Seniors, but also ties together the threads of 100 years of individuals’ lives,” Grayson says in a June interview. “It was the people who made the project—and the history. It was fascinating to see what life was like on the Cape before the turn of the century to the 1920s, and I wanted to capture that information before it disappears. It kind of creates a bygone era that we will never see again, but that is preserved in the pages of the book.”

Grayson’s book is packed with 100 years’ worth of marvelous photographs and great stories, including those of perhaps the most famous Wianno Senior of all—the Victura —and those who sailed her.

Crosby Yacht in Osterville is one of America’s oldest continuously running boatyards. Photo courtesy Jock Shafroth.

A compelling part of Cape Cod and American history, the Victura was the beloved Wianno Senior of John Fitzgerald Kennedy, which he began to sail as a 16-year-old during summers in Hyannisport. There are all kinds of stories floating around about JFK and the Victura , one of which relates that as president, Kennedy would frequently sketch his boat during Cabinet meetings, or when he was trying to solve an especially knotty issue, such as the Bay of Pigs crisis.

A story shared in another recent book, Victura: The Kennedys, A Sailboat, and the Sea by James Graham, says that on the day of his assassination, a maid cleaning a hotel room where JFK and Jackie Kennedy had rested for a few hours before the parade, found a small sketch of the President’s in a wastebasket. It showed a small sloop, sails flying.

Lucy Steere—one of those who shared some colorful stories about the Kennedys—says she believes the Wianno Senior played a pivotal role in launching JFK onto the national stage as it gave the young politician

the confidence and resourcefulness he would need to persevere through a grueling presidential campaign. “I really believe that sailing the boats and being accepted by everyone involved with the Seniors gave those boys the confidence to accomplish what they did in life,” says Steere.

This opinion was seconded by the late Senator Edward Kennedy in a video about the Seniors created by Fox News cameraman Andrew Fone—who also happens to be a Centerville resident and a lover of Wianno Seniors—titled “Lady of the Sound.”

In an ironic twist of fate, the Victura stayed safe and sound during a devastating event that destroyed much of the Senior fleet in December of 2003. A fast-moving fire burned much of Crosby Yacht Yard to the ground that night, including a storage shed housing 23 Wianno Seniors, some of which were antiques from the 1920s and 1930s.

One Wianno Yacht Club family—the Fallons—spent many an hour sailing with the Kennedys and skippering their own Seniors to nearly unparalleled success in weekly competitions and the class’ annual Edgartown Regatta race. John Fallon recalls the days when his father, Jack—one of the Seniors’ most colorful and skillful skippers—would routinely cruise past every contender to win trophy after trophy every summer. The elder Fallon, as a matter of fact, won nine Scudder Cup trophies, an annual award given to the skipper with the highest season-long record.

Photo Courtesy of Jock Shafroth

John Fallon, who sails and races his family’s boat, #199 Heritage , says the competitive spirit of the Wianno Seniors fleet was especially appealing to his father. “He was a very competitive person, as were a lot of the people who made up the fleet,” says Fallon. “They were all mavericks. My dad also loved the challenge of learning everything about the boat and doing everything he could do tomake the boat perform at its best.”

Ted Kennedy was one of Jack Fallon’s favorite sailors to spar with, whether during frequent practice sails or competitive races. John Fallon remembers long evenings when his father and Kennedy would keep sailing into the night. “Sometimes, I would go out with Dad in the evening, sailing against Senator Kennedy and his Senior,” John recalls. “They just wanted to practice and tune up and they would be out there when it was getting dark. As a teenager, I just wanted to be off with my friends— I’d be like, ‘Are we done yet?’ And Dad would say, ‘Just one more time up wind.’ They were just working the sails, fine tuning things, and trying to make the boats faster.”

Fallon says the two friends’ passion for Nantucket Sound and for sailing Wianno Seniors never seemed to abate, even when the weather turned cold and most Seniors were tucked away in Crosby’s sheds for the winter. “It was maybe a little crazy, the passion they shared,” says John. “They would be out there right up to Christmastime sailing . . . that was always the official end of the sailing season for them. When they got a little older, they finally started to end the season at Thanksgiving. The truth is they would go out on their Seniors and just stay out . . . they never wanted to come off the water.”

John Fallon is the skipper now of Heritage , showing his son the ropes on the family’s Senior. His son, Trey, is 15 and just getting his feet wet in racing, though he did win the Wianno Yacht Club’s juniors’ Commodore’s Cup two years ago. Asked to share his favorite Seniors moment, Fallon doesn’t hesitate.

“The memory that really put me in tears was the race two years ago when my son crewed for me,” he says. “I won the race that day with him on board. If I look back at winning three Scudder Cups and things like that, those are great memories too, I suppose. But what really comes back—my greatest joy— was having my son on board when I won that race.”

Still, that competitive Senior spirit simmers in this sailor whose family has won 12 Scudder Cups. “I did like the winning, too,” says John, who has won three Scudder Cups, “and it was a hell of a race. It was one of those times where it was very hard to stay up in front of the fleet and we were up front the whole time.”

For more Wianno Senior photos, visit capecodlife.com. For information on the Wianno Seniors’ 2014 100th anniversary celebration, including a Parade of Sail Friday through Sunday, July 25 to 27, visit wiannosenior.org.

Susan Dewey is the editor in chief of Cape Cod Life Publications. She grew up sailing on her family’s Herreshoff 15, #E8 Lazy Jack on the Mount Hope Bay.