Each year, as the days grow longer and warmer, the people of Chester begin preparation for the hectic summer months, when they will open up their tiny seaside community to visitors from miles and miles away.

 The warm ocean breezes, the sun and the surf attract everything from day trippers to weeklong sojourners and, every now and again, the sunny scenery and friendly locals work in tandem to convince the occasional family to buy a piece of the countryside to keep as their own.

 Of the many varying and eclectic inducements that bring people to the Village of Chester each year, there is arguably no more popular an event than the annual Chester Race Week.

 Every August, sailing enthusiasts from nearby and abroad bring their crafts and crews to the Chester Yacht Club to race on the waters of Mahone Bay. The briny adventures are just the beginning, as local restaurants, shops and businesses also swing into the spirit of the event and plan special gatherings to please the social movers among the race week crowd.

 But unlike many other events conjured up in the minds of the modern tourism planners, Chester Race Week, like the yacht club which hosts it, has a rich and long history. In fact, the record of the first major sailing regatta, the precursor of all future race weeks, goes back 150 years.

 In the late summer of 1856 an event remembered as the Grand Regatta was held in Chester. The regatta was a two-day event, held on September 4 and 5, a Thursday and Friday, and included seven classes of races, featuring different styles of craft and crew battling each other with the winds of the Chester back harbour in their sails.

 The first race pitted four-oared gigs against each other for a purse with golden accents, valued at $27.70. The contest was won by a four-man crew, including the three Naas brothers - Benjamin, Thomas and Joseph - and William Coolen.

 The quartet rowed a boat constructed by David Millet and succeeded in covering a distance of four miles in just under half an hour. The vessel was the first race boat Millet had tried to fashion on his own and he appropriately christened it First-step.

 In the second race, whale boats were featured. With whaling an important industry in the Atlantic ports of the mid-19th century, the battle of the four-oared rowers was a matter of pride among the foremost whalers. Ultimately, a boat and crew by the name Betsy took the top prize.

 The third race class was a battle of "flats." These craft, as their name indicates, were flat-bottomed boats designed for transporting cargo in the shallow coastal waters. The top three performers were the Lucy Short, the Lucy Long and the Eastern Belle.

 The fourth race involved punts rowed by boys under the age of 18 years. The top three boats were the Alma, the Silver Tip and the Flirt.

 The fifth race on the opening day at the Grand Regatta was the first event to feature sail-rigged vessels. In total, nine sailboats competed on open waters against each other over a 12-mile course.

 The winner of the fifth race was a vessel named the Katy Darling, owned by E.J. Robinson. Dr. Pearson, in the Secret, finished in second place, and B. McLachlan's Star took the third-place prize.

 For leading the pack, Robinson received a $24 prize and a silver cup. Pearson and McLachlan also received cash rewards for their efforts, collecting $16 and $8 pots respectively.

 The sixth race, and the final event held on the opening day, had an especially interesting historical twist: it featured a series of duelling canoes.

 The contest paid homage to the place of the canoe in early colonial contact, the major role the structurally simplistic craft played in the transportation of goods for the local Mi'kmaq peoples and early European settlers in Lunenburg County, and the strength and paddling techniques that had to be perfected to be the fastest on the water.

 After a series of races, Thomas Hammond and his mates took first place in the canoeing competition, with Nicholas Paul and his mates finishing a close second place.

 The seventh and final race of the Grand Regatta was held on the second day of the event, September 5, and involved 11 sailboats on an open-water, 12-mile course. In the grand finale, Dr. Pearson's Secret won first prize, claiming a silver cup and a $20 prize.

 The runners-up were the Quickstep, sailed by John Hyson, and the Mayflower, under Nathan Eisnor. The two captains received $12 and $4 purses each for their efforts.

 Needless to say, the racing on the water attracted much attention. In fact, it was estimated that more than 3,000 people crowded the shorelines to observe the racing on the second day of the Grand Regatta.

 But, much like the modern Chester Race Week, the Grand Regatta of 1856 had more to offer than tacking and turning on the water. The regatta also featured a number of social gatherings to delight the senses of both visitors and locals.

 Among the highlights of the weekend were a torchlight procession through the town and a display of fireworks that illuminated the settlement with a colourful hue.

 All told, the Grand Regatta was a huge success - so much so that in the years that followed, it served to inspire additional sailing and rowing competitions, even enticing local women to compete on the waterways.

 In 1858, a crew of four women - Annie Richardson, Bessie Garrison, Mary Jane Smith and Belle Barry - sent out a friendly rowing challenge to a foursome comprised of Helen Richardson, Mary Kearny, Ellen Barry and Annie Porter.

 Each team even had their own rowing uniforms, with Annie Richardson and her crew decked out in white duds with blue trim. The female teams, with the assistance of male steersmen, rowed out a mile, circled around a moored boat serving as a marker, then rowed the returning mile, much to the delight and enthusiasm of the large crowd in attendance.

 Like during the regatta of 1856, and the racing events of future generations to come, following the race the combatants set aside their oars of war and a celebratory ball was given in honour of the participants at Mulgrave House.

 And so, some 150 years ago, the traditional activities of Chester Race Week, both competitive and social, were first established. Over the years, the experiences were emblazoned on the minds and hearts of locals and visitors alike, inspiring generation after generation to continue the tradition and preserve the essence of the first Grand Regatta.

 Sources: "History of the County of Lunenburg," Mather DesBrisay; the Chester Yacht Club; the Bridgewater Bulletin.

Written and researched by Patrick Hirtle.