Chester Yacht Club

The Chester Yacht Club commands one of the finest sailing venues in North America, nestled on the sparkling waters of Mahone Bay along Nova Scotia's South Shore. This camera captures the club's waterfront, where sleek keelboats bob at their moorings and sailors prepare for their next adventure among the bay's 365 islands—one for every day of the year, as locals proudly claim. The protected waters, steady breezes, and stunning scenery have made Chester a mecca for sailors since the yacht club's founding, drawing enthusiasts from across the continent.

Every August, this tranquil harbour transforms into one of sailing's most exciting battlegrounds during Chester Race Week, the largest keelboat regatta in Canada. For the second full week of August, competitors from all along the eastern seaboard descend on these waters, their colourful spinnakers dotting the bay as they race around courses set among the islands. The regatta has been a cherished tradition for generations, blending world-class competition with the warm hospitality that defines this quintessential Maritime village.

Chester itself traces its roots to 1759, when it was established as the Shoreham grant, though French fishermen had already recognized the harbour's appeal years earlier. Massachusetts settlers arrived in 1761, drawn by the same natural beauty that captivates visitors today—the historic clapboard buildings, the artists' studios tucked along quiet lanes, and the timeless rhythm of a community shaped by the sea. Whether watching the Wednesday night racing series, following the drama of Race Week, or simply enjoying a peaceful sunset over Mahone Bay, this view captures the essence of Maritime sailing culture at its finest.