Chester Race Week
Chester Race Week takes place Aug 12 - 15, 2026 (the 2027 edition runs Aug 11 - 14) in Chester, Canada. The dress code is Casual maritime. Bring warm layers and waterproofs regardless of the date, because coastal Nova Scotia can be cool and foggy in August and evenings on the water are cold. Free to attend; budget up to 800 EUR per person for hospitality and extras.
Atlantic Canada's largest keelboat regatta, run by the Chester Yacht Club in the island-strewn waters of Mahone Bay. Several fleets race over four days while the small clapboard village of Chester turns into a sailing town, with the social tent and the harbourfront doing most of the work in the evenings. It is relaxed, family-heavy and genuinely welcoming to visiting boats.
- When
- Aug 12 - 15, 2026 (the 2027 edition runs Aug 11 - 14)
- Where
- Chester, Canada
- Dress code
- Casual maritime. Bring warm layers and waterproofs regardless of the date, because coastal Nova Scotia can be cool and foggy in August and evenings on the water are cold.
- Cost
- Free to attend; budget up to 800 EUR per person for hospitality and extras.
- Weather
- 16 - 22C, mild Nova Scotia summer with sea breezes and frequent coastal fog
- When to book
- Chester has very few beds - book by spring or plan to stay in Lunenburg, Mahone Bay or Halifax; boat registration opens through the Chester Yacht Club in early summer
- Getting there
- YHZ (Halifax Stanfield), 60 min to Chester
- Where to stay
- Mecklenburgh Inn, Chester (small village inn, walkable to the harbour), Oak Island Resort, Western Shore (larger resort 25 min along Mahone Bay), Bluenose Lodge, Lunenburg (characterful base 30 min away)
- Official site
- https://chesterraceweek.com
How to attend
Spectating is free from the Chester waterfront, the Front Harbour shoreline and the roads around the point. Social-tent evenings and parties are open to the public for a modest cover charge, usually well under 50 EUR. To compete, register a keelboat through the Chester Yacht Club in advance; the fleet is a mix of local boats and visitors from New England and Quebec, and crew places are easy to pick up by asking at the club in the days before.
Watching from the Chester waterfront is free and the shoreside social evenings take a small cover charge at the door, so nothing is booked in advance.
Insider tip
Almost nobody stays in Chester itself - base yourself in Lunenburg or Mahone Bay and drive in. The Front Harbour shoreline and the village bandstand lawn give a full view of the starts without needing a boat.
Get inside Chester Race Week
Booking matters here: chester has very few beds - book by spring or plan to stay in Lunenburg, Mahone Bay or Halifax; boat registration opens through the Chester Yacht Club in early summer. Members track that window, what it really costs, and 573 more events across the season.
Free while in beta. One email when your invitation is ready, nothing else.