Among factors that make Nova Scotia “Canada’s Ocean Playground” is the Village of Chester, which effectively serves as eastern Canada’s Mecca of sailing. Not only is Chester perfectly positioned at the head of Mahone Bay with sweeping views and access to its beautiful waters and 365 islands, but is host of Chester Race Week, the largest keelboat regatta in Canada, and second-largest in all of North America. Recreational sailing has been a primary component of Chester’s heritage for well over 100 years, and many full-time and seasonal residents call Chester home distinctly because of the sailing.    

Given this focus on sailing, a fair question to ask is what is the ultimate Chester sailboat? A question that could serve as an apt topic for debate among Chester sailors during the long sailing-free months ahead. Little doubt that every sailor has an opinion, so I’ll get the debate rolling by rendering my own experiences with various contenders for the title of “ultimate Chester sailboat.”

I am fairly certain that I took my first sail ever on my parent’s Bluenose, hull number 46 and then named Kaila. I was five or six years old at the time and can report that I did not enjoy the experience at all. She leaked heartily, had to be bailed constantly, and totally freaked me out despite forewarning from my parents when she went atilt to heel—I just knew that we were gonna flip over and sink! I did eventually get over my fear of flipping, but can’t say that I took to sailing during those early years. The water was cold, the directions regarding what to do next confusing, and the heat and passion of the few races I went on a bit too much for my sensitive nature at that young age.

Which is too bad, as the Bluenose is definitely in the running as the “ultimate Chester sailboat.” Designed in 1946 by William J. Roué, the same guy who designed and built the iconic Bluenose schooner as featured on Canada’s dime, the first dozen or so 23-foot one-design class sloops were built at the Barkhouse Boatyard in East Chester. Other local builders, including the Stevens Boatyard in Chester, also began producing Bluenoses, with a total of 77 wooden versions of the boat produced in the 1940s and 1950s. In 1968, Roué granted rights to produce a fibreglass version of the boat to McVay Yachts out of Mahone Bay, and since then another 100 or so fibreglass versions have been produced, first by McVay, and then by other builders such as Herring Cove Marine, and two other boat builders in Ontario.

The Bluenose is a great daysailer, but it’s primarily known for its racing pedigree, which has been a staple in both Chester and Halifax since 1949. In fact, the Chester Bluenose fleet is the largest one-design keelboat fleet in Atlantic Canada, and the Chester Yacht Club hosts an active racing schedule from June to September, and alternates with Halifax the hosting of the annual Maritime Bluenose Championship. With such a large fleet, and an exceptionally robust Chester community of Bluenose sailors, the Bluenose would undoubtedly be named the “ultimate Chester sailboat” if the designation was based strictly on local sailor polling.

Many Chester old-timers might argue that the Chester C-Class sloops represent the “ultimate Chester sailboat.” Built starting in the mid-1930s in Heisler’s Boat Yard in Chester’s Back Harbour, these sleek, beautiful racer-cruisers—Eclipse, Ripple, Ohop, Mistral, Restless and Whim—quickly joined Chester’s other Universal Class wooden sailboats such as Hayseed and High Tide in winning numerous races for their owners. Even with the rise of faster plastic boats in the 1960s, ’70s and ’80s, the Chester C Class boats were considered the grande dames of Chester’s sailing season, and would continue to bring home the glory well into the first years of this century.

While Ben Heisler famously said that “if God had wanted fibreglass boats, he would have made fibreglass trees,” none of Chester’s iconic C Class boats were on the water this year. Fibreglass boats have definitely been dominating the waters of Chester of late, though there is a small fleet of “Classics,” along with the wooden Bluenoses, and a half dozen IODs (International One Design class), all of which continue to stir the souls of the old timers and anyone else who appreciates the beautiful lines and craftsmanship of these old wooden boats.

My own personal experience with Chester C Class racing was short lived. I was probably eight or nine years old when my parents decided to expose me to the joys of big boat racing and offered my services to Danny Blain, skipper of the Eclipse. Danny, who wrongly assumed that I must know something about sailing, put me on foredeck duty where not only was I scared to death that I’d be swept overboard—Eclipse had no lifelines—but I promptly screwed up every command given. I did not last long on foredeck, and wasn’t much better at following commands anywhere else he put me, either. While I didn’t gain any new appreciation for sailing during my short-lived apprenticeship, I pretty much learned every curse word in the book that I hadn’t already known, being the recipient or cause of the many he expressed that day. I did sail on Eclipse on rare occasions in subsequent seasons, though only as a last resort when Danny couldn’t find anyone else.

Despite the early setbacks in my sailing career, I did eventually garner a love and passion for sailing. I also found what for me is the “ultimate Chester sailboat.” That is an Ontario 32. Built starting in 1977 as a collaboration between Ontario Yachts and C&C Yachts, the Ontario 32 was designed as a rugged yet comfortable performance cruiser, and adopted many design elements considered novel for that time. With 11 feet of beam, she was one of the beamiest production cruising sailboats being built in her size. Combined with six feet and four inches of headroom, this gave her an expansive amount of below-deck space, and allowed for exceptional comfort down below that is enhanced by an inordinate amount of teak in the joinery work, as well as a cozy miniature wood stove.

The boat yard built 158 Ontario 32s between 1977 and 1986, and, up until a couple of years ago, there were four of them in the Chester area. Not sure where the others went, but I still love mine. With four and a half feet of shoal draft I can enjoy up-close and personal exploration of the coastline. And all that space and comfort means I can share the beauty of Nova Scotia’s coastline for extended periods with my family and friends, something I do on a regular basis. Perhaps the most notable expedition was marked by a week in the Bras d’Or Lakes with another couple and three kids in total, during which the kids managed to play hide-and-seek on board for hours one rainy day. 

My boat is no slouch on the race course, either, with a half dozen third place finishes in various races, and a third overall in the Cruising Class for one Race Week. And, in what I consider an important bonus feature not available with many larger sailboats, she is easy to handle, which allows me to take her out solo without the need for crew.

All in all, she is my ultimate Chester sailboat. And sure, the Bluenose class truly deserves the designation, and the Chester C Class honorary mention, but I wouldn’t trade my Ontario 32 for either of them.       

—Originally Published in the MacDonald Notebook