North America’s Largest Sailing Race Week

Chester Race Week

The Annual Fisherman’s regatta began in Chester, Nova Scotia over 150 years ago when fisherman first raced to the Halifax markets competing to sell their goods. It was hard work where the men woke up early and with bodies tempered by nature, learned from their own mistakes. Work was a must, and taking charge when weakness wasn’t an option lead to a trust in your brother, family, and your own autonomy. They used what they had and built what they didn’t, and teaching the young to do the same was part of their craft. If you didn’t have a voice, you could still stand your ground. A value was passed down through tradition that created able hands. Today, those hands carry the tradition forward into the Chester Race Week— the largest annual keelboat regatta race week in all of North America.

The Village of Chester was built by strong women and sturdy men. In 1782 the brave women of Chester dressed in red cloaks and marched around the blockhouse to resemble British soldiers, saving the village from a raid by American Privateers lying offshore. A testament to the teamwork that still holds true today. The volunteer-driven event has a full list of public-friendly functions with live music, delicious food, yacht races, as well as seminars from internationally renowned sailors, tacticians, boat builders and sailmakers. Beautifully built boats fill the harbours with a diversity of talent welcoming all levels to participate in this highly organized event, hosted by the Chester Yacht Club and joined by neighbouring clubs. Chester Race Week is made possible by the people in the community.

Volunteers were incredibly busy and helpful. As Holly said “All the people selling shirts, wrist bands and drink tickets at the booth (were available) at all hours over the four days.” Holly and Michael Dunn, were responsible for media relations. The other members of the organizing team included:
Pat Nelder - Co-Chair of Chester Race Week - Water
Cynthia Spraggs - Co-Chair of Chester Race Week - Land
Mary MacInnis - Sponsorship Director

Last Saturday, while gripping the ‘oh shit handle’ on the back of a Boston Whaler, I was reminded of a healthy respect for the ocean. Jack MacKinnon, a Chester Yacht Club tender operator, effortlessly navigated the boat through the rain, and wind. Jack casually looked back as the Whaler skipped over 5 foot waves and asked where we were from. When I said Ottawa, in an honest, but playful tone he responded, “Ever been on a boat before?” His accent brought a smile to my face. “Not like this, Jack!” I shouted nervously, squinting into the wind as the bright yellow sou’wester clung to my head in desperation. It occurred to me then, that the ocean teaches us through gripped fear that holds our presence with its enormous power, but to the seafarer it’s second nature. This year, over 1200 skilled mariners raced over 4 days in howling winds, with competition beckoning the curiosity of skippers even across the mighty Atlantic. Although, I was disappointed to discover there were no crew nor clubs representing Ontario, or Quebec. Two provinces with many sailors threaded throughout the St. Lawrence.

When each series of yachts lined up for their countdown, they orchestrated themselves as if there had been a visible start-line. The crew and their skipper could maneuver on a dime, and I marveled at the expertise. Names, lingo, and slang slung from the men and women aboard the boats while sails tightened to the wind. The shouting of friendly rivalry comes with a sense of social inclusion that makes you feel at home. Across Canada, East Coasters are known for their warm inclusiveness. At the end of each race day sailors relax on their boats having drinks and snacks. When sea legs loosen they wander, three sheets to the wind, to the Foc’sle, Nova Scotia's oldest pub, and The Rope Loft for food and celebration.

Whether you come for competition, or vacation in search of an authentic east-coast experience, set your sail to Chester, Nova Scotia and join in on the tradition. Sailors across Canada – heed the call and head to Nova Scotia for the 2018 Chester Race Week. ​