| Date | Day | Event | Time | Location | Dress Code |
| May 3 | Mon | Rosary in Our Lady's Grotto | 10AM | Our Lady's Grotto | |
| May 7 | Fri | LS Grandparents' Day | 9am | Athletic and Convocation Center | dress uniform required for lower school students |
| May 8 | Sat | Annual Spring Gala & Auction | 6pm | Manor House | |
| May 10 | Mon | Rosary in Our Lady's Grotto | 10AM | Our Lady's Grotto | |
| May 13 | Thu | Ascension Thursday & First Eucharist Liturgy | 10am | Athletic and Convocation Center | Dress uniform required |
| May 13 | Thu | CommonGround Lecture: "How to Talk to Your Kids About Sex" by Elizabeth Schroeder, Ed.D., MSW | The Pennington School | 7:30-9pm | |
| May 15 | Sat | Princeton Academy presents Godspell | 7pm | Stuart Little Theater at Stuart Country Day School | Admission is free! |
| May 16 | Sun | Princeton Academy presents Godspell | 7pm | Stuart Little Theater at Stuart Country Day School | Admission is free! |
| May 17 | Mon | Rosary in Our Lady's Grotto | 10AM | Our Lady's Grotto | |
| May 20 | Thu | New Parent Orientation | 7pm | Manor House | |
| May 22 | Sat | Household Treasure Sale | 8am - 1pm | Athletic & Convocation Center | |
| May 24 | Mon | Rosary in Our Lady's Grotto | 10AM | Our Lady's Grotto | |
| May 31 | Mon | School Closed - Memorial Day |
