May 2, 2023 @ 12:47:33 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Massachusetts State High School Championship | Unregistered-NESSA | State Championship | 2 Divisions | Official | 3/20 | |
| NESSA Team Racing Championship (Presidents Trophy) | Sail Maine | District Championship | Team | Official | 8/8 | |
| NESSA Girls' Championship (Herreshoff Trophy) | Bowdoin College | District Championship | 2 Divisions | Official | 9/15 | |
| Downeast Regatta | George Stevens Acade | State Championship | 2 Divisions | Official | 2/19 | |
| Herreshoff Qualifier - Milton | Milton Academy | District Champ Qualifier | 2 Divisions | Official | 3/10 | |
| O'Day Qualifier - Quincy | Milton/BCH | District Champ Qualifier | 2 Divisions | Official | 5/10 |