| Date | Day | Event | Time | Location | Dress Code |
| Sep 1 | Tue | Faculty In-Service Day | |||
| Sep 2 | Wed | Faculty In-Service Day | |||
| Sep 3 | Thu | Faculty In-Service Day | |||
| Sep 4 | Fri | Faculty In-Service Day | |||
| Sep 8 | Tue | Returning Students Classroom Visits & Orientation | LS 8:30 - 9:30am. MS grades 6,7,& 8: 8:30-9:30am. 5th grade returning students: 12:30 - 2:30pm | ||
| Sep 8 | Tue | New Student Orientation & Family BBQ | Lower School new students are invited to visit classrooms from 11am - noon. A barbeque for the entire family follows at noon. MS new students will follow the following schedule: 5th grade 11-2:30pm, including the BBQ; grades 6-8 10am - 1pm including the BBQ. | ||
| Sep 9 | Wed | Classes Begin for All Grades - JK-8! | |||
| Sep 10 | Thu | Fall Sports Season Begins | 3:15-4:45pm | Practice for Soccer A and B & Cross Country begin today. | |
| Sep 12 | Sat | 10th anniversary all-school celebration 2-6PM | 2-6PM | On the grounds of Princeton Academy | |
| Sep 14 | Mon | MS Back to School Night | 7pm | Athletic and Convocation Center | |
| Sep 16 | Wed | LS Back to School Night | 7pm | Athletic and Convocation Center | |
| Sep 18 | Fri | Mass of the Holy Spirit | 10am | Athletic and Convocation Center | Dress uniform required |
| Sep 21 | Mon | HS Placement Meeting for parents of 8th graders | 7pm | Manor House Gallery Room | |
| Sep 21 | Mon | Cross Country v. Chapin (Away) | 4:00pm | Greenway Meadow Park | |
| Sep 23 | Wed | Apple Day - Please wear a red shirt! | |||
| Sep 23 | Wed | Parent-Faculty Open Basketball | 6:30-8:30pm | Athletic and Convocation Center | |
| Sep 24 | Thu | Soccer (A/B) v. PDS (Away) | 3:30pm | Princeton Day School | |
| Sep 24 | Thu | Cross Country v. Trenton Charter/Newtown Friends/Foundation Academy (Home) | 4:00pm | Home | |
| Sep 25 | Fri | Soccer (A/B) v. Chapin (Away) | 3:30pm | Chapin School | |
| Sep 26 | Sat | LS Father and Son Event | 2-4pm | Grounds of Princeton Academy | |
| Sep 29 | Tue | Soccer (A/B) v. Newtown Friends (Home) | 3:45pm | Athletic Fields | |
| Sep 30 | Wed | School Picture Day | 8am - 2:30pm | Dress uniform required |