| | Event | When | Where |
| August |
| | New Day Student Picnic | 8/26/2008 | Conroy House |
| September |
| | International Students Register | 9/2/2008 | |
| | Boarding Students Register | 9/3/2008 | |
| | Day Students Register | 9/3/2008 | |
| | All School Orientation | 9/3/2008 | |
| | Formal Dinner | 9/7/2008 | |
| | Convocation (All students must attend) | 9/7/2008 | |
| | Grandparent's Day | 9/24/2008 | |
| October |
| | SAT's for Seniors | 10/4/2008 | |
| | Admissions Fall Open House | 10/11/2008 | |
| | Midterm | 10/13/2008 | |
| | PSAT's for Sophomores & Juniors | 10/15/2008 | |
| | Parents Weekend | 10/17/2008 | |
| | Parents Weekend | 10/18/2008 | |
| | Head's Weekend Begins After Athletic Commitment | 10/18/2008 | |
| | All Students Return | 10/21/2008 | |
| | Junior Class Trip | 10/27/2008 | |
| November |
| | SAT's for Seniors | 11/1/2008 | |
| | School Play | 11/14/2008 | |
| | School Play | 11/15/2008 | |
| | Science & History Exams | 11/19/2008 | |
| | English & Conflict Exams | 11/20/2008 | |
| | Foreign Language & Math Exams | 11/21/2008 | |
| | Thanksgiving Recess Begins After last Exam | 11/21/2008 | |
| December |
| | All Students Return | 12/1/2008 | |
| | SAT's for Seniors | 12/6/2008 | |
| | Holiday Reflections | 12/16/2008 | |
| | Winter Vacation Begins at End of Academic Day | 12/18/2008 | |
| January |
| | All Students Return | 1/5/2009 | |
| | Midterm | 1/20/2009 | |
| | SAT's for Juniors | 1/24/2009 | |
| | Freshmen Trip Begins After Sports | 1/24/2009 | |
| | Freshmen Trip Returns | 1/27/2009 | |
| February |
| | Head's Weekend Begins at End of Academic Day | 2/5/2009 | |
| | All Students Return | 2/9/2009 | |
| | School Musical | 2/20/2009 | |
| | School Musical | 2/21/2009 | |
| March |
| | Spring Break Begins at End of Academic Day | 3/4/2009 | |
| | All Students Return | 3/25/2009 | |
| April |
| | Gunnery Today | 4/17/2009 | |
| | Student Performance | 4/17/2009 | |
| | Gunnery Today | 4/18/2009 | |
| | Midterm | 4/24/2009 | |
| | Head's Weekend Begins After Athletic Commitment | 4/25/2009 | |
| | All Students Return | 4/28/2009 | |
| May |
| | SAT's for Juniors | 5/2/2009 | |
| | Founder's Day Regatta | 5/3/2009 | |
| | AP Exams | 5/4/2009 | |
| | AP Exams | 5/5/2009 | |
| | AP Exams | 5/6/2009 | |
| | AP Exams | 5/7/2009 | |
| | AP Exams | 5/8/2009 | |
| | Admissions Spring Open House | 5/9/2009 | |
| | AP Exams | 5/11/2009 | |
| | AP Exams | 5/12/2009 | |
| | AP Exams | 5/13/2009 | |
| | AP Exams | 5/14/2009 | |
| | Formal Dinner | 5/24/2009 | |
| | Baccalaureate (All Students Must Attend) | 5/24/2009 | |
| | Senior Exams | 5/25/2009 | |
| | Athletic Banquet | 5/25/2009 | |
| | Senior Exams | 5/26/2009 | |
| | Senior Banquet | 5/28/2009 | |
| | Prize Night | 5/28/2009 | |
| | Commencement | 5/29/2009 | |
| | Reading Morning for Underclassmen | 5/30/2009 | |
| | Math Exam | 5/30/2009 | |
| | Foreign Language & Conflict Exams | 5/31/2009 | |
| June |
| | English & History Exams | 6/1/2009 | |
| | Science Exam | 6/2/2009 | |