Chester Grows Up

What was once primarily a social event to celebrate the end of the ephemeral Nova Scotia summer has become a serious destination regatta for racers from throughout Canada and, increasingly, the world. A feature from our January 2010 issue

January 15, 2010

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, cafes-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.”

Michael Lovett| |**Situated on the Front Harbor at the head of Mahone Bay, Chester YC (above) has hosted the regatta now known as Chester Race Week since 1902. **|


This time, the crew that partied as a team also won as a team; thanks to some strong breezes, the 28,000-pound Festivus cruised to first place in the distance fleet. “Scary thought,” says Holden. “We may actually be taken seriously next year.”

Rick Thompson, a Bermuda native who summers in Chester, is leading the development of the local International One Design fleet. With class president Jordy Walker, Thompson is helping interested sailors acquire boats and join the summer racing series. Thompson hosted Walker and other Bermudian IOD sailors for Race Week and threw a party at his house for the classics fleet. “Nothing is nicer than to share a good thing with others,” he says.
This year, Thompson’s Race Week included a trip to the Chester Playhouse for a showing of “Rockbound,” a theatrical adaptation of a 1928 novel set on an island in Mahone Bay. “At Race Week, the combination of socializing and racing is really quite palatable,” says Thompson, whose Mighty Mo placed second in the classics fleet. “I’ve been to race weeks in places like Cowes and Bermuda. Chester’s a lot lower key.”

Thompson’s houseguest was impressed with his first taste of Race Week. “Chester really is a unique little town,” says Walker. “The place comes alive for Race Week. We really enjoyed the entertainment. The Hopping Penguins were always playing late into the night. “

One aspect of the regatta that has never needed help is the post-race scene at Chester YC, where the Keith’s IPA flows freely and the Hopping Penguins lay down a lively groove. The band got its start at a Race Week party 27 years ago and has toured Canada and Europe with its repertoire of hard-driving reggae and funk tunes. “Chester Race Week has been a way of life for us,” says Edwards. “We know it’s where we’re going to be the third week of August every summer. This year, we had four bandmembers racing every day.”

Singer/saxophonist Andrew Lordly and keyboard player Ian Mosher sailed on the C&C 39 Ceilidh, owned by Randy Stevens, Chester YC’s rear commodore. Stevens is a Race Week fixture, having competed regularly since 1974. He knows precisely why the regatta works, why, despite the sluggish economy, the 2009 event still attracted more than 100 boats. “The race management is good, but it’s more than that. It’s the Hopping Penguins. It’s the ambiance of the community, and what Chester has to offer. And it’s the bay itself-it’s just a great place to go racing.”

If Philippe Paturel has his way, Chester Race Week will become a regular stop for North America’s most competitive big-boat campaigns. “This is one of the great sailing havens that should be better known,” says Paturel, who skippered the Archambault 40 CIAO! and, as North American distributor for Aigle outdoor gear and Archambault Boats, served as an event sponsor. “I’m hoping that more boats from the States will come. That’s really the only thing that’s missing.”

Paturel is a native of Saint Pierre and Miquelon, a group of French islands south of Newfoundland. His fondness for Chester and the potential he saw for Race Week inspired him to purchase a house on the Back Harbor. He has taken it upon himself to raise the profile of the event by bringing in a top-notch, international crew and promoting intense, Corinthian racing. “It’s a good occasion to invite my friends from France and California to come in for the regatta,” he says. “Having two or three races each day, more time on the water, makes it worth coming.”

With world-class talent on board, CIAO! was the team to beat in the PHRF-1 division. The French-speaking crew battled all week against David Murphy’s J/122 Pugwash, based out of Westport, Conn.

“We had been to Chester the previous summer, cruising on our powerboat,” says Murphy. “Race Week was going on at the time. We enjoyed ourselves so much, we decided to come back and race. This year, the battle with CIAO! made it a lot of fun. We went head to head all week.”

At the start of Race 3, CIAO! and Pugwash approached the boat end of the line overlapped on starboard. CIAO! had the leeward advantage and the opportunity to shut the door on Pugwash. At the last second, with his rival on a collision course with the race committee, Paturel bore off slightly and let Murphy through. “I could have closed them out,” says Paturel, “But then they would have plowed right between the pontoons of the committee boat.”
CIAO! went on to win that race and the next, but Pugwash won the series. “We had a great week,” says Murphy, whose new J/122 won four of the seven events it entered in 2009. “Chester’s in such a beautiful part of the world. The water is ten degrees warmer than it is down in Maine, it’s relatively undeveloped, and it’s only an hour flight from Boston.”

Teams like CIAO! and Pugwash can’t help but raise the level of competition for all Race-Week sailors. Even Edwards, the drummer who yearns for the point-to-point racing of the past, admits that the more competitive format has its advantages. “This year was the first time in many years that I sailed with a truly serious crew,” he says about his experience as pitman aboard CIAO!. “Everyone was really focused, and I got the chance to get more involved. In past years, I’d be exhausted from the parties and I didn’t really care as much about the races. This year, competing at such a high level gave me a renewed energy for the sport.”

As Chester Race Week revives the racing spirits of its faithful and becomes a bigger and bigger blip on the radars of travelling teams, one thing does not change: the regatta is addictive. Nobody sails just one. Some racers have been hooked for decades. Others have only just recently made the discovery. But from here on out, they all have plans for the third week of August.


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