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Chester Race Week, a keelboat regatta, attracts sailors from across North America. (PAUL DARROW/GLOBE AND MAIL)
Chester Race Week, a keelboat regatta, attracts sailors from across North America. (PAUL DARROW/GLOBE AND MAIL)

Canada’s largest annual keelboat regatta livens quiet N.S. town Add to ...

For most of the year, Chester, N.S., is a quiet village of 1,300 that centres mostly on heritage and tourism.

Over the next few days, it will be the scene of an impassioned, if picturesque, battle.

The Chester Race Week sees 130 boats converge from around North America to compete in what is billed as Canada’s largest keelboat regatta. Sailors are drawn by the world-class competition, the reliable winds of Mahone Bay and its spectacular setting.

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During race week, which ends Saturday, the town will swell by another 2,000 people – and about $800,000 and $900,000 will be injected into its economy.

Not that it’s desperate for the cash, exactly. Chester is a wealthy village on Nova Scotia’s south shore – a summer playground for multimillionaires, including philanthropist Sir Christopher Ondaatje, who owns an island that looks out on to Chester’s front harbour. Then there’s lobster billionaire John Risley, whose home is believed to have 16 bathrooms.

Among the summer houses, there is one for sale for $2-million – and it doesn’t have central heating.

But beyond the riches, the town and the races are steeped in history: Chester was founded in in 1759, and the race began in 1856 – it has since survived world wars and deep depressions. There are 13 classes of boats, including the Bluenose class, sailboats designed at end of the Second World War by Halifax naval architect William Roué.

Around town, the joke is that real estate and landscaping are Chester’s biggest industries, as the population grows from about 1,300 in the winter to 2,500 in the summer. Rich Haligonians relocate to the shore along with Ontarians and many Americans, such as the Wurtses, whose family fortune was made in coal and steel in western Pennsylvania.

Father and son John and Topher Wurts are the fourth and fifth generation of the Wurts family from Philadelphia to spend their summers in Chester; they race Hayseed, an elegant wooden sailboat with a checkered past, acquired by John’s grandmother in 1924. Her Halifax owner lost interest in her and left her on a nearby Chester beach after he won it all in what sailors called a “blood money” match – a hugely serious best-of-seven series – against a similar sailboat.

This week, Topher, 46, is the crew’s tactician on the 101-year-old boat as it competes during four days of racing at Chester Race Week. John, 77, is racing against his son – skippering Virginia, the equally beautiful but smaller and younger sister of Hayseed.

“We hate each other’s guts,” jokes John, whose sailing stories are told with a salty tongue.

No money goes to the winners.

“They win trophies and bragging rights. People will spend tens of thousands of dollars to win a five-dollar cup,” says Chester Yacht Club commodore Randy Stevens, adding: “Some of it is a bit of a debauchery.”

The rum does flow at the local hot spots – the Fo’c’sle tavern and the Rope Loft – and there are even stories (though some locals say they are apocryphal), of empty champagne bottles bobbing in the front harbour after a night of partying.

“I always thought of it being like the Christmas of the summer,” says Brookes Diamond, who owns an entertainment company in Halifax and is a long-time summer resident of Chester. He competed in race week for 30 years, sailing on High Tide, a yacht built in the 1930s. He owned it with seven other people and stopped sailing it in 2000.

He called what he does “social racing.”

“In our particular case, it was something of a party boat,” he says. “But we did try. We certainly did give it our best shot.”

For several years, Mr. Diamond recalls that he and his fellow sailors were barred from discussing yacht racing at the Fo’c’sle because the stories of who won and who lost over the years became “so frequent and so loud.” Some say the debauchery has toned down over the past 15 years, but a few Chesterites still escape their village for race week.

Not Rick Foster, however. The real-estate agent, who owns a home in Chester, is not a sailor but takes his Boston Whaler out to the start line, anchors there and watches the crews set the sails and work the ropes for the best start. “There are three or four different starts in sequence and depending on the wind, it is every exciting to see who is first over the line when the gun sounds.”

John Curry, a retired surgeon from Halifax, has been chairman of race week for several years. This will likely be his last, giving him time to get back into the racing.

He first competed in 1954, racing on the Chester C-class sloop, Ripple, now owned by Christopher Ondaatje. Although Sir Christopher is on a river cruise on the Danube, his boat will be competing, sailing against the Hayseed and Virginia in the 14-boat Classic class.

Topher Wurts has a passion for the Classic class boats – and hopes to save these old, elegant wooden yachts from being chopped up (partly because they are so expensive to maintain). He saved Virginia, buying it from a non-profit organization in San Diego that was closing its doors. He put together a consortium to buy Seneca, a 1907 sloop by Nathanael Herreshoff, a world-renowned sailboat designer.

In 1974, his mother sold Hayseed to a Haligonian, and by the late 1980s it was beached. Topher found it in 1998 – and rallied his family to buy it for $30,000.

“The Hayseed has been a member of the Wurts family for five generations, so you learn to take care and love this lady, and those of her kind,“ he says. “It’s a bit quixotic, but these ladies can fly, too. It’s easy to love them when they love you back.”

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