Maine has several annual regattas for High School Sailing. They are listed below with details.
Casco Bay Open - hosted by SailMaine in the fall, Atlantic Coast Championship Qualifier (NESSA race)
Becton Cup - late fall, hosted by Maine Maritime. Girls State Champ regatta (non-NESSA)
Dick Levesque Maine State Team Race Championship - spring, hosted by SailMaine
Various schools host regattas during the fall and spring seasons. SailMaine typically hosts regattas on Saturdays and Sunday every weekend during (Varsity Sat, JV Sun). More info can be found at the NESSA website.