Chester Race Week

Chester Race Week is Canada's largest keelboat regatta and one of Nova Scotia's most celebrated sailing events, built on more than 150 years of tradition. Each August the village of Chester comes alive as competitive fleets gather off its shores to race in one of the most picturesque sailing venues in North America — and the 2026 edition, held August 12–15, was no exception.

The regatta attracted top talent across multiple classes, including J70s, J105s, and classic yachts, with racing close enough to shore for excellent spectator viewing. Onshore, the Chester Yacht Club anchored a lively program of social events, dinners, and festivities that turned Race Week into a full community celebration.

Watching the racing from the waterfront was free, and the village's shops, cafes, and harbour walks made it a great day out even for non-sailors. Chester is about an hour from Halifax and pairs perfectly with nearby Mahone Bay and Lunenburg. Lodging books up well in advance, so reserve early to be part of this quintessential Maritime sailing tradition next summer.

Make the most of your time in South Shore - pair Chester Race Week with our South Shore guide, Best Day Trips from Halifax, and Lunenburg UNESCO guide. They're each packed with itinerary ideas, local tips, and everything you need to extend your stay.