| Date | Day | Event | Time | Location | Dress Code |
| Oct 3 | Fri | First Friday Group | 9am | Manor House | |
| Oct 10 | Fri | Founders' Day | 2pm | Athletic and Convocation Center | |
| Oct 13 | Mon | Columbus Day - School Closed | |||
| Oct 15 | Wed | School Picture Day | 8am - 3pm | Manor House Gallery | Dress uniform required |
| Oct 17 | Fri | ERB Testing Grades 3-8 | |||
| Oct 18 | Sat | Paint Out | 10am - 1pm | Princeton Academy grounds | |
| Oct 18 | Sat | Admissions Open House | 10am - 12 noon | Manor House | |
| Oct 20 | Mon | Feast of Mater Prayer Service | 2pm | William E. Simon Chapel Library | Dress uniform required |
| Oct 20 | Mon | Dedication of Chapel and Mater Admirabilis Tapestry | 2pm | William E. Simon Chapel Library | |
| Oct 20 | Mon | ERB Testing Grades 3-8 | |||
| Oct 22 | Wed | ERB Testing Grades 3-8 | |||
| Oct 23 | Thu | Parent Teacher Conferences - No School | |||
| Oct 24 | Fri | Parent Teacher Conferences - No School | |||
| Oct 28 | Tue | Boys Learn Differently: a lecture presented by headmaster Olen Kalkus | 7:30pm | Manor House | |
| Oct 31 | Fri | LS Halloween Parade | 12:30pm | Front of Main Building |