Chester Race Week

Chester Race Week Join us for ATLANTIC YACHT SALES CHESTER RACE WEEK August 11 - 14, 2027 four fantastic days of action on the water and ashore. www.chesterraceweek.com

From competitive fleets and top-notch race management to live music, social events, and MORE! Largest Keel Boat Regatta in Canada! Largest 3+ Day Sailing Regatta in North America! Winner of Sailing Nova Scotia 2016 Regatta of the Year! With regattas dating back to 1856, Chester Race Week was named one of Sailing World magazine’s 14 greatest sailing events in North America.

08/29/2026

So excited. Just restored this shot from RW2002!!!
Going to be restoring all and sharing here.

08/29/2026
Repost Boss Lady What a week in Chester. A huge thank you to the Chester Race Week Race Committee and all of the volunte...
08/22/2026

Repost Boss Lady
What a week in Chester. A huge thank you to the Chester Race Week Race Committee and all of the volunteers who put so much time and effort into making the week happen.

The Boss Lady crew had a terrific time! Great racing, challenging conditions, plenty learned, and a lot of fun along the way. We really appreciated the warm welcome and the opportunity to be part of such a great sailing event.

Thanks, Chester. We’re already looking forward to coming back.

PHRFRacing NovaScotiaSailing ChesterNS SailingLife TeamBossLady

WISHING YOU COULD SEE ALL THE AMAZING ACTION?! We got you! And this post is just a samplin' of the AWESOME SHOTS from ou...
08/19/2026

WISHING YOU COULD SEE ALL THE AMAZING ACTION?! We got you! And this post is just a samplin' of the AWESOME SHOTS from out on the water and MORE on the SHORE!! Thanks to Dream Imagine Believe Photography and their stellar contingent of fantastic PHOTOGRAPHERS we're amassing the MOST AMAZING PHOTOS of Atlantic Yacht Sales Chester Race Week 2026. All you need to do is scan the QR code and you'll find them all there!

You can share any of the shots there on social media and PLEASE BE SURE TO TAG THE PHOTOGRAPHERS. AND if you wish to have prints made just reach out to the respective photographer and they'll take it from there!

💙⛵BIG BIG THANKS to our PHOTO BOAT SPONSORS!!!
and our very own

Repost Sailing Cordelia T35 Dreams really do come true! Who knew, when Nick and I met racing on Mischief 13 years ago, ...
08/18/2026

Repost Sailing Cordelia T35
Dreams really do come true! Who knew, when Nick and I met racing on Mischief 13 years ago, that we would not only have our own sailboat but that we would be racing her during Chester Race Week, the largest keelboat regatta in Canada.

We spent an incredible week last week with incredible people full of heart and passion for the sport and for racing our girl as best as we could! Tactics, maneuvers, navigation - all 👌👌👌

Nick did a great job as a first time skipper in the regatta, despite all the angst and stress that comes along with it!

Our only objective was to come out, sail, have fun, and hopefully not come in last! Mission accomplished! ⛵️🌞💪

Can’t wait ‘til next year!

Thank you to all the volunteers in Chester who made this a great event, and thank you to all the photoboats for catching every moment!

Address

Chester Yacht Club, 21 South Street
Chester, NS
B0J1J0

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