The 2018–19 winter break schedule is as follows:
- Exams begin on Monday, December 17, and will be completed by Thursday, December 20.
- Boarders will spend the afternoon of December 20 packing and cleaning before a mandatory boarding dinner and the Senior Holiday Chapel performance that evening.
- Day students stay on campus that afternoon (12/20) to help clean the academic buildings between 1 p.m. and 3 p.m. before beginning their winter break.
- Boarding students should depart on Friday, December 21, by 12 noon when houses close. There will be a bus to Logan Airport and South Station that departs at 9 a.m.
- Boarding students should plan to return on Monday, January 7, between 4 p.m. and 8 p.m. The bus will pick up at Logan Airport at 7 p.m. and at South Station at 7:15 p.m.
- Classes resume on Tuesday, January 8.