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A Class Act – Chesapeake’s Great Schooner Race

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Right after the Annapolis boat shows in October, about 40 salty-looking, two-masted  schooners take off from a starting line just south of the Chesapeake Bay Bridge and sail overnight 127 miles to Portsmouth/Norfolk. Welcome to the majestic fleet of the Great Chesapeake Bay Schooner Race, an annual event skippered by equally salty sailors.

A schooner can be separated from other sailboats by a front mast that is lower than the rear one. A few schooners have three or four masts.

The schooner has a particularly historic and appealing appearance. “When we started our cruise business,” says Captain Jen Kaye, owner of Schooner Woodwind in Annapolis, “we asked ourselves, what is the most romantic looking of sailing boats – a schooner or sloop?  The schooner won out and now there are two Woodwinds that take out 400 people a day in the harbor.” Woodwind is also a regular in the race.

The race looks like a clip out of the movie, “Captains Courageous.” There’s something about a schooner and specifically about the race that inspires a feeling of nostalgia for a nobler time. There is as much concern with sportsmanlike behavior and a code of safety as there is about the competition.

Great Chesapeake Schooner Race: One of the Bay’s Finest Traditions

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It all started in 1989 when Capt. Lane Briggs, a charismatic sailor with white mutton-chop sideburns and a moustache, challenged Jan Miles, the skipper of Pride of Baltimore II to a race. It was to be a race reflecting the historical competition for trade in the early 1900s between two ports in the Bay: Baltimore in Maryland and Portsmouth/Norfolk in Virginia. The original schooners were workboats and the fastest ones got the cargo business.

Reflecting his unorthodox and creative personality, Briggs boat, Norfolk Rebel, was actually a tug retrofitted as a schooner. He called it a “Tugantine,” since it was inspired by the Brigantines, which are historic, gaff rigged schooners.

Briggs’ personality was a magnet for others to join in the race over the years, making it a significant event in both ports. This year’s events take place Oct. 13 to 19. The schooners begin arriving early in the week, docking at the Baltimore Marine Center. Many are open to visitors. Wednesday evening the schooners participate in a parade of sail around Baltimore’s Inner Harbor.

An Appreciation of Wintertime

The race officially starts about 1 p.m., Thurs., Oct. 16, just south of the Bay Bridge. Participating schooners have a handicapped rating and are divided into four classes. They race against the others in the same class, as well as against the entire fleet for bragging rights. Vessels report in at various times throughout the night for safety and verification of time-taken reasons. All schooners can be tracked throughout the race at www.schoonerrace.org. The race usually takes about 20 hours and the record for finishing was made in 11 hours and 18 minutes in 2007 by the schooner Virginia.

Weather during the race is classic for the Chesapeake. It can be the doldrums, squally with walls of rain or perfect winds for sailing. It’s almost a Zen-like experience to hear participants talk or write about the race. One blogger describes “a moonset that looked like a tangerine slice melting into the dark black sea.” Another writes about the dark night “with phosphorescence churned up by white caps.”

Some of the best observations have come from guest cruisers. Susan Helbert, a retired law enforcement worker, calls herself “Frequent Sailor Susan” because she’s been on Woodwind, 350 times. Having done the race a few times, she describes the experience as “screaming down the Bay with the current, slicing through the water in silence with only the sound of the wind and waves. It’s truly the grandest adventure I’ve ever been on. It requires you to be in the present moment.”

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Capt. Aram Nersesian, a highly-respected captain, has raced every year since 1996 on Heron, a 60-foot schooner. Nersesian stresses the youth educational part of the schooner events as being as much of a reward to him as the racing. The proceeds of the race are donated to support children’s education programs of the Chesapeake Bay Foundation.

Mark Faulstick, captain of schooner Adventurer, a 65 footer with a 7-1/2 ft. draft, takes a crew of nine for the race. Faulstick is another regular in the race and, for years, has brought his boat from Connecticut to participate.

“About 30 percent of the race participants are from outside the Bay and it takes a lot of work for these boats to come. Many continue on down to the Caribbean for the winter.

“The race can be challenging, especially with a large fleet of these boats heading down the Bay at once. One time a front came through and we had 50 to 60 knots of wind,” says Faulstick. “Most went for cover.”

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Built in 1926 as a yacht for a Mystic, Conn. doctor, Adventurer was 70% rebuilt in the 90s.

“I bought her after I crossed the Atlantic on a schooner and was impressed with its seaworthiness. They are impressive boats and they draw a lot of attention,” says Faulstick. “Once, while [I was] in a Maine harbor at breakfast, a diner who had seen the boat at anchor said, ‘breakfast on me for the prettiest boat in the harbor.’”

As with most successful boating activities, there is a strong contingent of loyal volunteers who make the Great Chesapeake Bay Schooner Race live up to being great. Out of the race (and associated activities) comes a sense of family and lifetime friendships. “There are a lot of hugs,” says Faulstick.

25th Anniversary of the Great Chesapeake Bay Schooner Race

October 13 -14
Schooners begin arriving at the Baltimore Marine Center. Some will be open to the public.

October 15
10:00 am – 2:00 pm
Schooners open to public (Canton)

5:00 pm
Parade of Boats can be seen from the Canton, Fells Point, Harbor East and Inner Harbor shorelines.

October 16
8:30 am – noon
Schooners make their way from Baltimore to the start line south of the Chesapeake Bay Bridge.

1:00 pm
The Great Chesapeake Bay Schooner Race Start

October 17 
Race Finish:
The finish line for classes A and AA is an east-west line at Thimble Shoal Light.
Classes B and C finish at Windmill Point. All schooners then proceed to docking in Portsmouth.

October 18
Public viewing and education programs throughout the day (Portsmouth) Award dinner (by invitation only)

October 19
Watch as schooners begin leaving Portsmouth for their next destination.

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Vicki Lathom
Vicki Lathom
Vicki lives in Annapolis, MD, where she and partner, Barry Miller, cruise the Chesapeake and the Intercoastal Waterway to the Bahamas or Florida. They cruise in a 36-foot Albine Express trawler named, Balboita.

So Caribbean you can almost taste the rum...

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