[8] At times, the academy has billed itself as the oldest continuously operating boarding school in the United States.

Although William Dummer was not a college graduate, his brother Jeremiah attended Harvard and provided important early support to Yale.

[13] It was "the first school of its kind in America" to operate on-campus residential facilities for boarders,[14] who comprised the remaining one-third of the student body and lived in Governor Dummer's old mansion.

[13] (Today, "Mansion House" serves as the headmaster's residence and plays a regular role in student life.)

The curriculum focused on instruction in Latin, Greek, and the classics, with supplemental teaching in sacred studies, basic math, and English.

[18]) During the early republican era, the term "academy" typically signaled an institution's intention to broaden the academic curriculum beyond Latin and Greek.

As a result, Dummer Academy became stabilized and began to again thrive as a premier New England prep school that sent over a third of its graduates to Ivy League colleges during that period.

"[23] Some students and alumni resisted the change, questioning why the academy should let "shallow" teenage jokes supersede tradition.