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Chester Race Week

August 13-16 2025

“Canada’s largest keelboat regatta,” Race Week offers an unsurpassed racing venue. Hundreds of participants and spectators enjoy the races and the on-shore entertainment, and sailors from all over Canada and the States attend every year.

Yacht racing has been a major summer sport in Chester for well over 150 years. Its roots are firmly planted in the mid-19th century when the fishermen raced each other to markets in Halifax or New England.

The first documented regatta was in 1856. 

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Photo of the Chester Yacht Club during Chester Race Week with tents, people, boats, and music.