Photo by Muffy Aldrich
The Modern Guide to The Thing Before Preppy

Wednesday, November 2, 2022

The New England Headmaster's Walk

Photo by Salt Water New England

The New England prep school headmaster's walk is immediately identifiable.  When walking from office to dining hall, for example, it combines two elements.

The first is surveying the quad.  What is the mood?  Is there a productive hum or is there a pervasive dourness?  By the third week of school, the headmaster has deliberately memorized the names of all the students, and is getting a feel for individual temperaments.  Likely the headmaster will make two or three engaging and knowing comments on the five minute trek.  

The second is the stoop.  The headmaster habitually looks for scraps of paper or other debris to scoop down upon and pick up.  By the time the headmaster reaches the dining hall, there is a handful ready for depositing in the proper receptacle by the entrance.  

And this is done every step of every day during the headmaster's reign.  


  1. And so it was in the south as well. Rest in peace, James Buckner Massey.

  2. Replies
    1. Middlesex in Concord, Massachusetts

  3. Our headmaster selected a sixth form boy to be the Senior Prefect each semester. When I was "SP" he and I spent every Sunday evening after dinner discussing the state of the school from each of our perspectives. This was during the cultural ferment of the late 1960s, a disruptive era. Those evenings in his study were the most engaging and important experiences of my entire time at the school and lead in part to the school going coed.

  4. And magically appears scratching his chin at the first sign of rambunctiousness.


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