| Halloween Fleet Race | Tabor Academy | Promotional | 2 Divisions | | Pending | 7,8/13 |
| 2026 NESSA Great Oaks Qualifier | Sharon | In-District | 1 Division | | Official | 11/16 |
| Roy Williams Invitational | St. George's | In-District | 2 Divisions | | Official | 12/18 |
| Fall FunFest | Sharon High School | In-District | 2 Divisions | | Official | 10/17 |
| Wakeman 3D Fleet Race | Tabor Academy | Promotional | 3 Divisions | | Official | 6/9 |
| Arnold Brown Regatta | Marthas Vineyard Reg | In-District | 2 Divisions | | Official | 5/12 |
| Casco Bay Open | Portland | In-District | 2 Divisions | | Official | 4/11 |