Chester Race Week 2025

A sailing regatta and celebration with lively entertainment. Watch exciting sailing races and enjoy the social scene with bbqs, dances, live music with bands.

Since the sea gives Chester its character, sailing naturally occupies a position of importance here. 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 Helly Hansen Chester Race Week event takes place over 4 days and attracts participating yachts and crews from across Canada. This year we are expecting over 140 boats to participate in the various classes on several race courses in Mahone Bay. The event is the most significant sporting and community event in the region with many sailing related workshops & demonstrations, as well as participation by local artisans, merchants, and food providers. There are also popular social activities throughout including the nightly live music events.