Windsor’s youth and their elders packed the John Fitch High School auditorium to witness the 1944 Halloween costume judging contest for grade school students. Lipstick, shoe polish, and burnt cork were used to paint their faces.
A total of 36 prizes were awarded for the most original and the most comical costumes.
Members of the High School Dramatic Club put on a play for the audience after the prizes were awarded. Following the costume judging and the play, Windsor teenagers held a Halloween dance at the town hall, which they took over from the court officials who postponed court proceedings until the next day.
According to Windsor Police Chief Paul Rustic, damage to property on Halloween night totaled less than $25, or about $325 in today’s money.