The population of the tiny maritime community of Chester swells every summer, when the annual influx of well-heeled vacationers takes place. Chester’s yachting and entertaining season attracts visitors from all over North America.
A lonely cloud floated across the sapphire sky and 20-m.p.h. winds churned the muscular seas. Conditions, in short, were ideal for sailing. And the only real concern last week, as the wooden and fibreglass sailboats circled Mahone Bay off Chester on Nova Scotia’s south shore, was whether Ben Heisler could muster enough strength to fire the cannon to start the race. Now 87, the fabled Nova Scotian boat builder is pipe-cleaner-thin, with a face like a piece of brown wrinkled leather. Old age and 30 years of shooting the starter’s gun have left him stone deaf. “Not sure how much longer he’ll be up to it,” conceded one race organizer. But today, fortified with rum and coke, he sat in the bow of the race committee boat, gamely struggling to load the heavy brass cannon. After a couple of misfires, a bang finally rang out. Seconds later, their brightly colored spinnaker sails billowing, the first members of the fleet roared past the starting mark. Chester Race Week–the most celebrated week in Atlantic Canada’s most celebrated summer village–was officially under way.
Ask any local and they will say that Chester has only two seasons: summer and the rest of the year. Most of the time, it remains just another quiet village nestled on Nova Scotia’s postcard-perfect south-west coastline. Quieter than most, actually: unlike the neighboring fishing and boat-building towns, Chester offers limited year-round employment; sky-high real estate prices– by Nova Scotian standards–make it expensive for people to live there and commute to jobs in Halifax, 70 km to the east.
But come June, Chester blossoms like the perennials in its many well-tended gardens. The influx of summer folk, from all over eastern North America, swells the village’s population of 1,000 by as much as 30 per cent–and gives the otherwise sluggish local economy a welcome jolt. Chester is Georgian Bay without the heavy traffic, the Hamptons minus the New York City crowds. Jaguars, Mercedes, BMWs and Saabs–many with Ontario, Quebec, Pennsylvania and Maryland plates–purr through the winding, leafy streets. Gleaming yachts skirt the nearly 200 tufted islands that dot the bay. At night, laughter floats from inside the village’s bars and restaurants and soft lights brighten the interiors of the grand old homes that sit dark throughout the long winter. “There’s a timeless quality to this place,” says Charles Ritchie, 87, Canada’s former ambassador to the United Nations and London, who has been summering in Chester for 25 years, “a most agreeable rhythm of parties, entertaining and informal visits which you find yourself falling into.”
That may be the case today. But Chester, founded in 1761 by New England settlers, was a real backwater until some wealthy Philadelphians “discovered it” a century ago. As recently as 1942, U.S. travel writer Dorothy Duncan labelled Chester “an American colony,” serving as a summer haven to descendants of former president Grover Cleveland and a bevy of presidents of American universities. Even now, descendants of the old American families make their annual pilgrimage.
So do the Canadian summer folk: wealthy developers, businessmen and lawyers from Halifax as well as such national notables as Tory Senator Finlay MacDonald, former federal cabinet minister Barbara McDougall and Christopher Ondaatje, the exotic Sri Lankan-born financier, author and adventurer who bought the struggling Chester Playhouse and donated it to the town two years ago. “None of the people who come here want to make a buck out of Chester,” explains Ondaatje, 61, who lives on a 100-acre island in Mahone Bay and spends the rest of the year in London and Bermuda. The same, it seems, holds true for those who own summer homes in the neighboring coves, inlets and hamlets such as former federal Liberal party president Donald Johnston who was spotted dining in the Seaside Shanty in the town of Chester Basin this summer with former prime minister Pierre Trudeau and Quebec novelist Mordecai Richler. The summer folk do their best not to antagonize the year-round natives. Sitting on his veranda, which provides an ample view of the bay, Desmond Piers–a retired rear admiral in the Canadian navy who has been summering in Chester for 75 years–says the two factions get along famously. “The summer people are here because they like to sail and they want to enjoy the beauty,” the vibrant 81-year-old maintains. “To a person they’re quiet and discreet.”
That point is amply demonstrated by the late 19th- and early 20th-century homes owned by the summer visitors. Despite their elaborate names–Morning Tide, Pinecroft, Westerleigh–many of the houses hide their manicured gardens and expansive verandas behind wooden fences and thick hedges. That, of course, does not mean that Chester lacks excitement. This year, the village was aflutter over the Hollywood film adaptation of the Stephen King novel Dolores Claiborne, shot at the white-pillared waterfront mansion owned by retired Halifax developer John Fiske. Chester has its eccentrics too, although few can match Col. Jack Miller, a Scottish lumber merchant and golf aficionado who moved to Chester in 1910. When his youngest child and wife died, Miller had them buried by the third hole at the Chester golf club, which he then owned.
All in all, Race Week–a fixture since 1904–may be the only time the village truly cuts loose. While many local boats compete, the majority of the 80 vessels and roughly 500 crew members who descended on the village last week were from other ports in the Maritimes, Ontario and New England. The village was largely silent during the day as the boats tacked and gybed, but by cocktail hour the 94-year-old yacht club was rocking to a loud reggae beat. “We’re not trying to have an Olympic-style regatta,” declared the club’s rear commodore Dan Blain, 57, as he sipped rum at the end of the wharf. A Florida resident who says he “did well during the Reagan years,” Blain summers in a home that has been in his family for more than a century. “The idea,” Blain added, “is to enjoy the great sailing and have some fun.”
Not too much, though. Veteran competitors long ago christened the week-long event “Chester Waste Week.” This year’s committee hoped to keep the legendary partying under control. As the night wore on, the sunburned stock brokers, doctors, factory workers and college students who packed the Fo’c’sle, Chester’s oldest and most popular watering hole, began to shed their self-restraint. “They’re sailors,” reported Tim Matthews, the Fo’c’sle’s part- owner. “They drink one hell of a lot of rum.” But it was a pair of brawling skateboarders who smashed through the tavern’s window around 4 the next morning.
By then, even the most determined partyers were resting for the new day’s race. Come mid-morning, a few could be glimpsed at Julien’s Pastry Shop wolfing down croissants and cappuccino. Eventually, the first groggy-headed sailors arrived at the yacht club, dropped into big wooden chairs on the front deck and stared out at the bay. “I went to university in the south of France,” said Suzanne Risley, a single mother of one who splits her time between Halifax and Chester, “and not even the Mediterranean can rival Chester, in the summer.”
But already the morning air carried the first hint of fall. Race Week, as well as being the peak of Chester’s summer, also signals the season’s approaching end. Soon the boats come out of the water, homes are locked for the winter. All that will remain of Race Week is the memory of bright sails snapping in the wind beneath a startling, pale blue sky.