Chester Yacht Club bluenotes racing upwind

By Katherine Stone

You won’t find a prettier site in all of Canada (although I am sure that the west coast sailors would probably disagree!) nestled on the Chester Peninsula extending into Mahone Bay along the south shore of Nova Scotia, with both a front and back natural harbour. The bay is dotted with about enough islands for each day of the year. The village was founded in 1759 during the French and Indian War. Setters from New England were given Shoreham land grants for the area we now know as Chester and the Tancook Islands. These people were known as Planters, as they farmed the land and were also fishermen. During the American Revolution, some Yankee privateers tried to plunder Chester. The men were off fighting the war, however, the women of Chester, armed with broomsticks and wearing their red-lined cloaks inside out, marched along the shore convincing the privateers that the village was substantially fortified. They soon gave up and went down the way to plunder Lunenburg instead. This would not be the last time that the women would lead the way in this sailing community. It naturally followed that by 1791, the major occupation would become boat building. Fisherman, wanting to be the first to market in Halifax or New England, would start to race each other to get there first! Soon after, they started to race for sport and the Annual Fisherman’s Regatta began.

Chester Yacht Club - Chester Back Harbour sunsetAn excerpt from the History of Chester chronicles the beginning of the present day Chester Race Week, the largest keelboat regatta in Canada now held every year in the second week of August. “On Sept. 4th 1856, a grand regatta was held at Chester… this became a yearly event for quite some time to come. This first regatta…was quite an event with more than 3,000 persons present. There were seven different boat races conducted ranging from gigs of 4 oars, flats, punts, canoes and sail-boats. The winners all getting prizes of money.” Not surprisingly, the population in Chester from 1861-1911 grew by 93%, but the boats grew by 400%! Chester had become a summer resort hotspot for the American market. Hotels, like the Hackmatack, and boarding houses were in abundance, along with boats for pleasure sailing to islands for picnics and racing. Fishing captains were hired to race fine double ended whalers with tan coloured sails boiled in spruce gum, bark and tar Chester had become the Newport of the north. Neither was it an abode of wealth or fashion, but  just a summer resort to keep cool, relax, and live informally.

Chester Yacht Club bluenotes preparing to race, 2012By 1900 Dr. Keasbey, from Byrn Mawr, PA  had gathered some like-minded men and drawn up a constitution, by-laws, sailing rules, and race schedules to form a yacht club and start and end races off Robinson’s Wharf. Dues would be $2. Incorporated in 1902, the club charter stated, “The object of the club shall be to promote yacht building and sailing, and to encourage its members in becoming proficient in navigation in the personal management, control, and handling of their yachts and in all other matters pertaining to seamanship.”  Chester Yacht Club’s emphasis was always to be on racing, with the first boat to cross the line winning – ratings were unheard of and you would always have some big, burly men on board who would shift the ballast from one side of the boat to the other to get full advantage.

Sadly, WWI changed Chester Yacht Club. Men could no longer take summer long holidays. Stays became shorter and 2,000 guests each season were no more. Women became the leaders in the summer community, owned yachts, sailed yachts, and were now active in running the club. 

Chester Yacht Club aerial viewFinally, in 1924 the board accepted a proposal to lease with purchase privilege, the Hilchey property on which was a boat shed. The local citizens pitched in and built the wharf on which stood the flagpole from which races were started and finished up until 2000. Now with 110 members, dues were raised to $5 and by 1928 they owned the property. The ladies also became very instrumental in organizing fundraisers for the club, as it was becoming more apparent that the membership numbers could no longer support the upkeep of the clubhouse and the wharf – which seemed to get destroyed by winter storms almost every year. 

From 1925 to 1935 saw a notable increase in the number of competent sailors and high quality boats. By 1936 the Chester C Class had been launched which was an excellent “small” boat (37 feet) for cruising as well as racing. This rise of remarkable seamanship was soon to end, as the sailing committee soon noticed that the elementary rules of yacht racing were being ignored resulting in unfair advantages and damage to yachts.  Each boat was soon issued a set or rules and the sailing committee illustrated them to members on the blackboard. Wednesday afternoon races were becoming so popular that stores closed their doors after lunch so that sailors could be available to race and spectators could line the wharf and shoreline.

Chester Yacht Club's Andreas JosenhansWWII and the automobile ended forever the long summer stays by American families. During the war, 44 Chester homes were made available for medical rest. The club wisely realized during the war that it would cost as much to close the club as to remain open. The men were away at war, so dues were not paid. In 1944 the sailing committee consisted of ladies who were the sailors and the executive. They ran fundraisers from bingo to card parties, to Sunday afternoon teas, which were highly successful for the cash flow of the club. At that time, ladies  wore  their “whites” sailing (clothing, hats, and gloves). Funny how the ladies still wear hats, albeit baseball ones, and gloves, now without fingers! Families now needed a boat that was smaller and easier for women and children to sail.

The Bluenose Fleet of 20-25 boats now has a very active multi day racing program at CYC. It is also the largest one design fleet in Nova Scotia.The first Bluenose was built in East Chester. A team of oxen hauled it to the water where it was launched in 1946. Designed by William Roue, a Nova Scotian boat designer and at 23 feet in length, it fit the bill perfectly as a family racer/day cruiser. The size allowed 2-3 sailors to handle it, young and old, men and women at a reasonable cost. 

Chester Yacht Club trophies on displayBy the 1950s the clubhouse was expanded and the Junior sailors were at the helm of their own boats (model boats and the Bluenose). An instructor was hired in 1966 and sailing school started with a few Cadets, soon moving to Flying Juniors. Today, the sailing school boasts a Wet Feet program and, Optimists and 420s with racing teams in both fleets.  The clubhouse saw a major facelift in 1968 and was restored in 2006. 

The women’s Ratting of Teacups kept this little club afloat through the hard times. The strong presence of women at the helm during both wars, was to lay the foundation for a very community oriented club. Mrs. Wurts and Mrs. Starr would keep a vigilant eye on all goings on at the club, perched on the veranda in their broad brimmed black hats and long black dresses. 

Mary MacInnis, long time member, permanent resident of Chester, and past Chairman of Chester Race Week put it simply, “Chester Race Week is about the fun – come for the sailing and stay for the fun, or vice versa! The regatta has survived because sponsors make it happen and volunteers make it work and because the sailors love it.” The Hopping Penguins band has played at CRW for the past 25 years – each time for a sell-out crowd. ” 

Dr. John Curry, member since the 1970s, also a full time resident of Chester and former chairman of Chester Race Week also noted that they are, “No different than any other yacht club in NS other than they attract Olympians like Paul Tingley, Lisa Ross and Andres Josenhans who have all sailed Bluenoses.”

This club has more membership categories than you can shake a stick at – something for everyone. Now more than 110 years old, the history of this club was chronicled in the book Sailors and Rattling Teacups. After reading the wonderful account I totally understand how much influence the rattling teacups had on this club.  The book’s introduction put it succinctly, “Sailboat racing has records, people have wonderful memories. Unfortunately, they don’t always agree.” Sounds like Karate Chop sailing at the bar to me!

Rattle your way down to the south shore of Nova Scotia and you’ll find a wonderful group of fun loving, laid back people who have done just about anything to keep their (it is one of the largest in NS) club alive and well, and who also  just love to spend time on the water.


Chester Yacht Club; P.O. Box 290; Chester, NS  B0J 1J0 (902)275-3747



Photo 1 - Bluenoses racing upwind.

Photo 2 - Chester Back Harbour at sunset.

Photo 3 - Bluenoses preparing to race 2012.

Photo 4 - Aerial view of the Chester Yacht Club.

Photo 5 - Andreas Josenhans during on of his famous pre-race tactics talks.

Photo 6 - Famous Chester trophies on display above the bar.