2026 Race Schedule
Fleet Day
Six weekends of highly competitive racing in 2026
The Chesapeake 20s are traveling again for the first time in nearly a decade! Our first travel event will be to Tred Avon Yacht Club's Heritage Regatta which will serve as our "Nationals".
Note that additional racing will be had through West River Sailing Club's Sunday Series.
Want to meet the fleet?
The fleet will be participating in Fleet Swap Fridays hosted by West River Sailing Club, Severn Sailing Association, and Eastport Yacht Club. On Fridays in June, you'll be able to experience a lot of one-design fleets available in this area of the Chesapeake Bay.
May 30-31st
Tune Up Regatta
Saturday Work Day on the fleet, followed by a day of racing on Sunday.
June 6-7th
Dave Irey Regatta
Two day regatta at WRSC
June 27-28th
West River Heritage Regatta
We're hosting a Heritage Regatta with WRSC. Saturday is our traditional Heritage Race with Round-the-Buoys on Sunday
August 22-23rd
Nationals at TAYC
The Twenties are traveling again! Our first travel event in nearly a decade will be the Oxford Heritage Regatta hosted by Tred Avon Yacht Club.
September 4-6th
West River One-Design Weekend
The Annapolis to Galesville Race followed by the 97th Annual Regatta at WRSC.
September 26-27th
Dick Hartge Cup
The season closer celebrating our Class history.