Skip to main content

Bay Tripper

Junior Fleet is more than just sailing

Junior Fleet is more than just sailing

There is no place on Chesapeake Bay quite like Gibson Island, a unique private community developed in the 1920s by famed New England landscapers for wealthy Marylanders as a watery retreat from torrid Baltimore summers of old.


 The Junior Fleet is a Gibson Island Yacht Squadron tradition that dates to 1924.

The emphasis during those early island days was on sailing and golf, in that order because the water was in place but golf was not. Today there is a nine-hole course, and many other sports are offered, including tennis and swimming. A large, protected harbor serves as a seasonal mooring field for resident boat owners inside a gated barrier causeway that also keeps the Bay at bay.

The Junior Fleet of the Gibson Island Yacht Squadron is a sailing tradition that goes back to 1924 when the driving spirit for the next 25 years was Nathaniel S. “Cap” Kenney. He was ably assisted by the tough and rugged George R. “Salty” Marks, a close friend, teacher, rigger and the first island harbormaster.

A retired Navy chief bosun’s mate, Marks lived in a harborside cottage and work shed crammed with rigging tools, canvas, rope and other yacht paraphernalia. He died in 1963 at the age of 83 after falling on a large anchor stored in his cottage. The preserved “Salty Marks House” is now the home of the Gibson Island Historical Society and museum.

Cap Kenney conducted his sailing lessons in the harbor boathouse and inaugurated a gala Junior Fleet banquet at the Gibson Island Club, where a “Best Boy” or later a “Best Girl” had his or her name inscribed on a huge silver punch bowl. The permanent Symington Trophy is named after the island’s founder and developer, Judge W. Stuart Symington Jr. Best Boy of the 2008 season was Noah Baily, 13, also a 2007 winner, whose name will be entered on a plaque.

In those early days, outdoor recreation on the island focused on teaching the sport to the Junior Fleet members of the Gibson Island Yacht Squadron. Many of those youths went on to offshore racing and winning sailing championships and Bay regattas. One of those distinguished junior sailors, Richard (Jud) Henderson, 84, of Annapolis, is the author of “Chesapeake Sails: A History of Yachting on the Bay,” published in 1999 by Tidewater Publishers, of Centreville, Md.

In the book he also recalls his own personal memories of “halcyon days at GibsonIsland” during which he spent some summers living with his family aboard their 35-foot yawl, Kelpie, on a harbor mooring. They weren’t the only summer liveaboards during those Depression years of the 1930s.

The rich tradition of the Junior Fleet continues, and the season concludes every August with the annual Dobbins Island Race Back in 420s. In years past, prior to Dobbins being purchased by a new owner who posted and fenced the beach with no-trespassing signs, prerace events included a picnic on the beach. In a “Grand Prix” start, crews sprinted to their beached boats, rigged them, and off they went, back to Gibson Island’s protected harbor about a mile away.

After the race, more tradition dictates that costumed parents take over the 420s for a short “Ma and Pa Race” in the GibsonIsland harbor. Participants run a watery gauntlet and are doused from the docks by a younger crowd armed with buckets, water guns and hoses. These good times conclude with a cocktail party and a harbormaster’s cookout on the boathouse grounds.

To cover this event in proper yachting fashion, I sailed my boat, Erewhon, a dozen or so miles north from Annapolis to the 1,000-acre island, where home sales begin at $1.8 million. I overnighted at the dock as a guest of harbormaster Capt. Denver Sanner in order to be on hand for the next day’s festivities.

That evening, I hitched a ride in a golf cart to the informal clubhouse grill, where I dined (on a member’s tab) on large softshell crabs gently pan-fried in butter, a traditional summer dish. After dinner, I relaxed Bay-side in a traditional GibsonIsland lawn chair at sunset, imagining myself savoring a frosted mint julep of fine Kentucky bourbon in a silver goblet, enveloped in the pale-blue haze of a good cigar and cool salt air.

The next morning I stood by as Capt. Sanner continued his tradition of firing a shotgun into the air at 8 a.m. as a wake-up call. He marks his 25th season as harbormaster next summer. I motored in a chase boat to join the Junior Fleet members and their parents on a beach at the island’s sandbar point at the mouth of the MagothyRiver on the Bay’s WesternShore. There, boats were rigged, and carefully folded sails were unfurled and run up the masts.

I joined Scott Williamson, director of the summer program, and two of his instructors, John Strong and Charlotte Tracy. After a buoy was set at one end of the starting line, the five-boat race was on. It took a while for skippers to nail down a meandering whisper of a confused wind, which will be made easier next summer when the 420s might be equipped with masthead wind vanes.

After the start, we were joined by Walter Mitchell, vice commodore of the yacht squadron and chairman of the Junior Fleet Committee, who took the helm. Williamson, a Latin teacher in Baltimore, went beyond shouting encouragement to the racers, and at first there seemed to be a difference of opinion between the two men on coaching or not coaching during what Mitchell regarded as a trophy race.

“Let them race! Let them race!” pleaded Mitchell. Williamson, whose teaching background took over, shouted advice on trim, where to head, and warnings of lurking sandbars. I was a bit surprised the fleet didn’t sail better after their summer of camp and sailing lessons, especially among those tending jib sheets. But I’m accustomed to dodging the hotshot tots of the Severn Sailing Association, racing Opti prams off Annapolis and managing quite well in light and heavy air, knowing exactly what to do and when.

“Our program is filled with novice sailors, and geared toward enjoying the pleasures of the water and sailing,” Williamson explains. “Our youths don’t have much interest in racing at this point in their lives. The program focuses on building lifelong sailors and having fun on the water versus winning races, which might come later.”

On average, about 30 boys and girls ranging in age from 8 to 13 participate in the June to August program. To enroll, they must be children or grandchildren of club members, although guests of youths can be included.

Kip Strong, in his very first race, was the winning skipper in the August outing. Crewmember Connor Kennedy had never been in a 420 before, and when they crossed the finish line, he shouted, “I never expected this to happen!”

Next to finish were skipper Madison Sentimore and her sister, Taylor. Madison filed a surprise protest she later withdrew in a good sportsmanlike gesture when she was informed the skipper of the offending boat could be disqualified.

In third place were skipper Aubrey Barringer and crew Gilbert Sentimore, followed by Katie Schluederberg and Erin Barringer. In last place were the Goldsborough brothers, Nigel and Charlie, who at times seemed to lose their sense of direction until course corrections came from coach Williamson.

In the Ma and Pa Race, bearded Gibson Island Yachtsman J.P. Watson in a hula outfit recruited Aubrey Barringer as crew. (You might remember J.P. from last month’s column.) They were drenched with water barrages in the dock area and missed a turning mark. “I had water in my eyes,” was the excuse of the burly Watson, who fell into the drink upon landing and temporarily lost his sunglasses before finding them on the murky bottom.

Chairman Mitchell thought the on-land water barrage “got a bit out of hand” at the dock and may be discontinued at next August’s adult portion of the end-of-season event. Barringer, embarrassed by Skippy Watson’s clumsiness, kept his balance and cool.

“Aubrey is totally hooked on sailing and also crews for coach Williamson in regattas,” says his father, Jim, who has mastered the family Sunfish.

After the race, Aubrey, 12, expressed a desire to board my 22-footer, a Sparkman & Stephens-

designed fiberglass classic built in Holland in 1962. I have never seen anyone spend so much time in my small cabin before, taking it all in and quietly looking into every nook and cranny. After climbing out of the boat, he said to his father, “We must get a boat like this.”

A week later, during a breezy southerly, I was tacking toward the mouth of Back Creek off Annapolis, careful to avoid a small fleet of Penguins, when I became aware of someone shouting and waving at me. It was Aubrey in a Penguin, and he had recognized my Erewhon.

Jack Sherwood is writer at large for Soundings.