| Question | |
| Which current Millbrook faculty couple met while teaching at Cheshire Academy? | |
| What current Millbrook faculty couple met while teaching at Berkshire School? | |
| What current Millbrook faculty couple met while teaching here at Millbrook School? | |
| Where was the school theater before the Chelsea Morrison Theater was built? | |
| What was the first dormitory to be built on campus? | |
| Name the 3 prizes that are awarded on commencement morning. | |
| Name the 3 prizes that are awarded on commencement morning. | |
| Name the 3 prizes that are awarded on commencement morning. | |
| Name the first formal ceremony that all students and faculty participate in at the beginning of the each school year. | |
| What is the name of the short ceremony that all new Millbrook students attend in the Chapel on their first night on campus? | |
| What is the name of the service we celebrate at Millbrook just before Winter Break that occurs right about the time of the Winter Solstice and a variety of religious holidays? | |
| What was Edward Pullings nickname? | |
| Who is the first Chairman of the Board of Trustees, and has a portrait in the library? | |