Winchester Grange holds two regular meetings a month, on the second and fourth Tuesdays, unless otherwise noted. Prevailing time is 7:00 PM. For evenings where a Potluck Supper is held, the evening will begin at 6:00 PM, and the meeting will follow.

Historically, Winchester Grange holds conferrals for membership each April and September. Installation of Officers is also held each September, with Election of Officers held annually in June.