1911
Tom Ashley, local farmboy, Deerfield icon, US Marine, and friend and collaborator of Mr. Boyden, graduates. After attending Amherst College and graduating in 1916, he returns to the Academy as a teacher, coach, and advisor to Mr. Boyden. Ashley is credited with establishing the Academy’s boarding department and drafting its first school catalog. In 1918, he is killed in action at the Battle of Belleau Wood.

1916
John Williams House, aka, the house that features the Academy’s famous Door, is renovated into a dorm.
1918
Sunday Sings begin a long tradition of song at the Academy.
1921
The Deerfield Cup is established honoring that individial from each class that best embodies the values of Deerfield Acadamy.
1922
The first Deerfield-Choate football game is played. (Go Big Green!)
1939
The first train to Choate, carrying athletes, students, and faculty
1962
The Deerfield Medal is established.
1968
Mr Boyden retires.
Mrs. Boyden retires.
1989
Deerfield returns to coeducation