Tim Wilkes

With 25 boats, the Bluenose class, which originated in Nova Scotia in the 1940s had the largest fleet at 2009 Chester Race Week.

Chester, Nova Scotia, was originally a fishing town. In the 1800s, profit and pride pitted the town's fishermen against rivals from nearby Lunenburg and the islands of Big Tancook and Little Tancook across Mahone Bay; they raced their cod-laden schooners to market in Halifax, 40 miles to the east, and New England, 500 miles to the southwest. In 1856, the competition became official. Thousands of spectators turned out for the Grand Regatta, which featured not just sailing and rowing races, but a torch-lit parade and other land-based amusements. By 1885, the annual regatta included a circus and a hand-cranked Ferris wheel.

Despite these auspicious beginnings, Chester Race Week-it was renamed in the 1950s-remained a local event, an end-of-summer bash with some leisurely distance races thrown in for the sake of sobriety.

"I sailed my first Chester Race Week when I was 19 with an old fishing captain out of Lunenburg," says 51-year-old Gary Edwards, a summer resident of Big Tancook and drummer with the Hopping Penguins, Race Week's house band. "The event used to be all week long before they trimmed it down to fit people's schedules. Thursday was a lay day, Friday we'd race down to Lunenburg, and then Saturday we'd race back to Chester for lunch. It was more of a reaching parade than anything else. To me, that was the essence. I miss that side of it."

The event Edwards grew up on began to change in 2006, when Chester Race Week experienced a re-awakening. While it has retained much of its folksy charm, the regatta has been recast in a more modern light, with multiple windward-leeward races each day, a top-flight race committee, and a more compact schedule. The change has been dramatic. Three years later, Chester Race Week is simultaneously Canada's biggest keelboat event and North America's best-kept secret.

With its narrow streets sloping down to the water, meticulously restored captains' houses, and cluster of art galleries, organic markets, cafés-even a playhouse-the town of Chester (pop. 1,500) is an intimate retreat for well-heeled families from as far off as Virginia. At the bottom of the hill sits Chester YC, which overlooks the cruising boats and classic yachts moored in the Front Harbor and, beyond that, Mahone Bay, a relatively protected sailing area ringed by 356 islands-one for every day of the year, locals like to say. Chester's largest estates line the craggy, pine-studded shoreline of its Back Harbor and the rolling lawns of its southern peninsula. The place is summer Shangri-La, and until a few years ago, Race Week was just another one of its seasonal pastimes. Locals took the competition no more seriously than they would a round of croquet.

In 2006, sailmaker Andreas Josenhans, a resident of Lunenburg, went out to watch a day of racing. The Olympic and America's Cup veteran was unimpressed with what he saw. "I was looking at it going, 'Hmm. I wonder if that could be done better,'" says Josenhans. "Of course, I knew if I opened my big fat mouth, I'd have to follow through with it."

Nonetheless, Josenhans did just that. He went before the regatta's stewards at Chester YC and proposed a number of improvements to the racing format. Working with logistics guru Mary MacInnis, the Race Week chair, Josenhans transformed the regatta into a professionally run, four-day, around-the-buoys event with racing on three circles for everything from classic yachts to Bluenose one-designs to IRC-optimized raceboats.

Nowhere is Josenhans' fresh approach to race management more evident than in his thundering pre- and post-race pep talks. Disappointed by what he'd seen on Day 1 of the 2009 event-an egregious mid-line sag, boats crossing the line minutes after the gun-the burly 59-year-old gathered competitors on the dock in front of Chester YC prior to the second day of racing. In the kindest possible way, he told the competitors that they, well, stunk on Day 1. He proceeded to share tips for how to carve out a hole, how to hit the line with speed-in general, how not to stink.

Under Josenhans' watch, even the most casual racing boats are starting to come around. Mark Holden, a former goaltender for the Montreal Canadiens, only started sailing four years ago. His Beneteau 49 Festivus is Race Week's undisputed party boat, with mixed drinks down below and bikinis on deck. As the regatta has grown more competitive, Holden's team has followed suit. "I'm an impulsive guy," says the 52-year-old Halifax resident. "I jumped right in to the racing thing. I've asked a million questions over the last few years, and I feel like we've come light years as a team. We're even starting to shake some of that party-boat reputation."

He did say some of the aforementioned reputation. After the first day of racing, Festivus tied up to its customary dock by the Rope Loft, Race Week's favorite watering hole. On stage were the Hopping Penguins, and revelers spread from the bar to the stage to the boat. "We had so many people onboard we started gaining waterline," says Holden. "The dock beside us began to sink. It turned into a pretty fun time. And for us, that's the bottom line.

"What I miss about hockey is what I've regained with sailing. It's the camaraderie. You win as a team, you lose as a team, you party as a team."