| 4/8/20 |
Virtual Sailing Regatta Series (every Thursday in April) |
| 5/7/20 |
Virtual Sailing Regatta Series (every Thursday in May) |
| 5/6-9/30/20 |
START DATE TBA: Wednesday Night Fleet Racing at Sagamore YC |
| 6/7/20 |
Sunday Racing (every Sunday through October 4th) |
| 6/13/20 |
POSTPONED DATE TBA: Squaw Cup |
| 6/17/20 |
Ladies Sailing Series Racing (every Wednesday through September 23rd) |
| 6/21/20 |
Alfred Roosevelt Regatta |
| 6/26/20 |
Summer Solstice Series (every Friday through August 14th) |
| 6/28/20 |
Cayenne Trophy Series ( 1 of 2) |
| 7/4/20 |
Junior-Senior Challenge |
| 7/11-7/12/20 |
Annual Rendezvous |
| 7/15/20 |
Kiwassa Cup |
| 7/25-8/2/20 |
Eastern Cruise |
| 8/1/20 |
Dooley Roosevelt Regatta |
| 9/5/20 |
Stratford Shoal Race |
| 9/6/20 |
Fall Regatta (One-Designs) |
| 9/7/20 |
Fall Regatta (PHRF) |
| 9/12/20 |
Elihu Root Trophy |
| 9/16/20 |
Benzie Cup |
| 10/3-10/4/20 |
Middle Sound Race |
| 10/4/20 |
Cayenne Trophy Series (2 of 2) |