| 4/3/21 |
District 8 Spring Fling Regatta |
| 4/17/21 |
Oyster Bay Challenge |
| 5/5- |
Wednesday Night Fleet Racing at Sagamore YC |
| 5/8/21 |
Alfred Roosevelt Regatta |
| 5/23-5/24/21 |
Kathleen Trophy (TENTATIVE) |
| 5/29-5/30/21 |
Outlaw Trophy |
| 6/2/21 |
Ladies Sailing Series Racing (every Wednesday through ) |
| 6/6/21 |
Sunday Racing Series (every Sunday through |
| 6/19-6/20/21 |
Commodore Swan Cup |
| 6/25/21 |
Summer Solstice Series (every Friday through August 13th) |
| 6/26/21 |
Squaw Cup |
| 6/27/21 |
Cayenne Trophy (1/3) |
| 7/4/21 |
Junior Senior Challenge |
| 7/10-7/11/21 |
Annual Rendezvous |
| 7/13/7/17/21 |
Commodores' International Cup |
| 7/14/21 |
Kiwassa Cup |
| 7/24-7/25/21 |
Corinthian Young Guns |
| 7/24-7/31/21 |
Eastern Cruise |
| 8/7/21 |
Dooley Roosevelt Regatta |
| 8/15/21 |
Cayenne Trophy (2/3) |
| 8/27-8/29/21 |
Islands International Challenge Cup |
| 9/1-9/4/21 |
Thompson Cup |
| 9/4/21 |
Stratford Shoal Race |
| 9/5/21 |
Fall Regatta (One Designs) |
| 9/6/21 |
Fall Regatta (PHRF) |
| 9/11-9/12/21 |
Morgan Cup (Ladies Sailing) |
| 9/15/21 |
Benzie Cup |
| 9/18/21 |
Elihu Root Trophy |
| 9/25-9/26/21 |
Seawanhaka Invitational for the Cruise Cup |
| 10/3/21 |
Cayenne Trophy (3/3) |
| 10/9-10/11/21 |
Lee Family Trophy |
| 10/13-10/16/21 |
British-American Cup |
| 11/7/21 |
Moosehead Luncheon |