| Time | | | Event | | |
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| 6:00 PM | | | WNR Series 1 Weeknight racing at its best! | | |
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| 11:00 AM | | | AYC Spring One Design Regatta Drop Marks courses for one design classes | | |
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| 6:00 PM | | | WNR Series 1 Weeknight racing at its best! | | |
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| 11:00 AM | | | Helly Hansen Sailing World Regatta The Annapolis stopover for the series with multiple divisions for one design classes and a two-day distance race. | | |
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| 11:00 AM | | | Helly Hansen Sailing World Regatta The Annapolis stopover for the series with multiple divisions for one design classes and a two-day distance race. | | |
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| 11:00 AM | | | Helly Hansen Sailing World Regatta The Annapolis stopover for the series with multiple divisions for one design classes and a two-day distance race. | | |
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| 6:00 PM | | | WNR Series 1 Weeknight racing at its best! | | |
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| 12:00 AM | | | Spring Race to Oxford Point to point race starting in Annapolis and ending in Oxford. Tred Avon YC hosts the post-race social and awards party | | |
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| 11:00 AM | | | Spring Harbor Regatta The Harbor 20 Class spring event | | |
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| 6:00 PM | | | WNR Series 1 Weeknight racing at its best! | | |
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| 6:00 PM | | | WNR Series 1 Weeknight racing at its best! | | |
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| 6:00 PM | | | WNR Series 1 Weeknight racing at its best! | | |
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| 6:00 PM | | | WNR Series 2 Weeknight racing at its best | | |
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| 12:00 AM | | | Don Backe Memorial CRAB Regatta | | |
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| 6:00 PM | | | WNR Series 2 Weeknight racing at its best | | |
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| 12:00 AM | | | MD Cures Cancer Regatta This regatta includes top notch competition on the water and for fundraising. Organized by Eastport YC and supported with course management, by AYC Race Committee | | |
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| 6:00 PM | | | WNR Series 2 Weeknight racing at its best | | |
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| 6:00 PM | | | WNR Series 2 Weeknight racing at its best | | |
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| 12:00 AM | | | AYC Jr. Annual Regatta Summer regatta for junior sailors - includes Opti Green, Red, White & Blue, 420s and ILCA Classes | | |
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| 12:00 AM | | | WNR LayDay July 4th holiday break | | |
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| 6:00 PM | | | WNR Series 2 Weeknight racing at its best | | |
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| 6:00 PM | | | WNR Series 2 Weeknight racing at its best | | |
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| 6:00 PM | | | WNR Series 3 | | |
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| 11:00 AM | | | AYC Annual Regatta 88th Running of AYC's Annual Regatta sailed over 2 days for OD and ORC classes | | |
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| 11:00 AM | | | AYC Annual Regatta 88th Running of AYC's Annual Regatta sailed over 2 days for OD and ORC classes | | |
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| 6:00 PM | | | WNR Series 3 | | |
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| 11:00 AM | | | AYC Two Bridge Fiasco Open to single and doublehanded entries who sail in either direction on the course that includes the Bay Bridge and Naval Academy Bridge | | |
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| 6:00 PM | | | WNR Series 3 | | |
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| 6:00 PM | | | WNR Series 3 | | |
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| 6:00 PM | | | WNR Series 3 | | |
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| 6:00 PM | | | WNR Series 3 | | |
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| 12:00 AM | | | Annapolis Labor Day Regatta Hosted by AYC in 2024 with course management assistance from EYC | | |
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| 7:00 PM | | | WNR Awards Party Awards party and trophy presentation for 2024 WNR Series 1, 2 & 3 | | |
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| 12:00 PM | | | Harbor 20 East-West Championship Class event with competitors representing both coasts. Fleets represented: California, Florida, South Carolina and Annapolis | | |
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| 12:00 PM | | | Harbor 20 East-West Championship Class event with competitors representing both coasts. Fleets represented: California, Florida, South Carolina and Annapolis | | |
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| 12:00 PM | | | Harbor 20 East-West Championship Class event with competitors representing both coasts. Fleets represented: California, Florida, South Carolina and Annapolis | | |
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| 12:00 PM | | | Harbor 20 East-West Championship Class event with competitors representing both coasts. Fleets represented: California, Florida, South Carolina and Annapolis | | |
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| 12:00 AM | | | Annapolis YC 3-2-1 Invitational AYC's signature team & match racing event. The Invitational welcomes 7 visiting teams to AYC to compete along with Team AYC | | |
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| 12:00 AM | | | Annapolis YC 3-2-1 Invitational AYC's signature team & match racing event. The Invitational welcomes 7 visiting teams to AYC to compete along with Team AYC | | |
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| 9:00 AM | | | AYC Fall Race to Solomons A fall favorite, point to point race beginning outside of Annapolis Harbor and ending near Solomons Island | | |
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| 12:00 AM | | | Annapolis YC 3-2-1 Invitational AYC's signature team & match racing event. The Invitational welcomes 7 visiting teams to AYC to compete along with Team AYC | | |
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| 12:00 AM | | | Cal 25 Nationals 2024 Cal 25 Nationals includes one stand alone race day and two days during Fall Series | | |
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| 12:00 AM | | | Cal 25 Nationals 2024 Cal 25 Nationals includes one stand alone race day and two days during Fall Series | | |
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| 12:00 AM | | | Cal 25 Nationals 2024 Cal 25 Nationals includes one stand alone race day and two days during Fall Series | | |
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| 11:00 AM | | | AYC Fall Series - Weekend 1 Small One Design Classes | | |
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| 12:00 AM | | | Cal 25 Nationals 2024 Cal 25 Nationals includes one stand alone race day and two days during Fall Series | | |
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| 11:00 AM | | | AYC Fall Series - Weekend 1 Small One Design Classes | | |
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| 11:00 AM | | | AYC Fall Series - Weekend 2 Includes ORC and J/105 on Bay Course with Harbor 20s on River Course | | |
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| 11:00 AM | | | AYC Fall Series - Weekend 2 Includes ORC and J/105 on Bay Course with Harbor 20s on River Course | | |
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| 8:00 AM-5:00 PM | | | Warrior Sailing | | |
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| 8:00 AM-5:00 PM | | | Warrior Sailing | | |
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| 8:00 AM-5:00 PM | | | Warrior Sailing | | |
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| 11:00 AM | | | J/105 Chesapeake Bay Championship Fall class championship | | |
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| 11:00 AM | | | J/105 Chesapeake Bay Championship Fall class championship | | |
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| 8:00 AM | | | AYC Halloween Howl Fall Junior regatta for Opti Green, Red, White & Blue, 420 and ILCA classes | | |
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| 8:00 AM | | | AYC Halloween Howl Fall Junior regatta for Opti Green, Red, White & Blue, 420 and ILCA classes | | |
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| 12:00 PM | | | AYC Frostbite Series - 1st Half | | |
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| 12:00 PM | | | AYC Frostbite Series - 1st Half | | |
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| 12:00 PM | | | AYC Frostbite Series - 1st Half | | |
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| 12:00 PM | | | AYC Frostbite Series - 1st Half | | |
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| 12:00 PM | | | AYC Frostbite Series - 1st Half | | |
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| 12:00 PM | | | AYC Frostbite Series - 1st Half | | |
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| 12:00 PM | | | AYC Frostbite Series - 1st Half | | |
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| 1:00 PM | | | AYC Hangover Bowl Kick off the New Year on the water | | |
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