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2025 Race Schedule
Fleet Day
Six weekends of highly competitive racing in 2025.
Note that additional racing will be had through West River Sailing Club's Sunday Series.
On the Saturday of the West River Heritage Regatta, June 21st, the Chesapeake 20s will be having an open house.
This will be a fantastic opportunity to meet the fleet, see the boats, and even get to sail on a Twenty. Not only will you get to see the Twenties, but you'll be able to see all of the other hertiage classes
May 10-11th
Tune Up Regatta
Saturday Work Day on the fleet, followed by a Mother's Day Brunch on Sunday with an afternoon race.
June 7-8th
Dave Irey Regatta
Two day regatta at WRSC
June 20-22nd
West River Heritage Regatta
We're hosting a Heritage Regatta with WRSC. Saturday is our traditional Heritage Race with Round-the-Buoys on Sunday
July 12-13th
Worlds
Who has the fastest Twenty in the world? Well we'll find out. Every boat chooses a country to represent and shares a dish inspired by the country in our post-racing potluck tradition.
August 29-31st
West River One-Design Weekend
The Annapolis to Galesville Race followed by the 96th Annual Regatta at WRSC.
September 27-28th
Dick Hartge Cup
The season closer celebrating our Class history.
Find a Boat!
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