First Fridays are events held on the first Friday evening of each month that school is in session. First Fridays and dances are open to all middle school students and provide them with the requested time together to socialize outside of school hours. Permission slips are required for day students. Beginning in the 2016-17 school year, all middle school day students have dorm assignments, so they are able to stay on campus and get ready for these special events with their boarding friends. First Fridays have included athletic events, dances, movies, games, pep rallies, and bonfires.

The Black and Orange rivalry is a decades-old tradition at The Rectory School. Each student and faculty member are assigned to either the black team or the orange team. Once a term, they compete against each other in a variety of different activities. Academic and effort grades are factored in as well to determine an overall winner each term. Whichever team wins, at least, two terms is that year’s winner! An official plaque representing the color of the winning team hangs outside the Headmaster’s office for the year!

During the months of January and February, Rectory students have the opportunity to hit the slopes of Wachusett Mountain, in Princeton, Massachusetts, every Sunday for some skiing or snowboarding. Both day and boarding students are welcomed to sign up for the fun! Applications for the 7-week program are available beginning in October and are due to the Director of Student Activities by mid-November.