Reverend James R Hugh served as headmaster of the Academy from 1868 to 1900. He was succeeded by his son James Hugh, who operated the school until it had to temporarily close during the leanest years of the Great Depression.
Not only was the Academy known for its excellence in education but also for its excellence in sports. In 1908 the Academy beat Penn State in football which lead the team to go to the playoffs and eventually win the National Prep School Championship.
The Academy educated numerous governors and politicians, including Andrew Curtin and Rev John Palmer. The Academy caught on fire in 1904, but the school trustees were able to not only repair the damage, but add a third floor to the building along with an improvement to the front of the building. After the Great Depression, the building was converted into an apartment building. After the building was destroyed by fire in 2004, the only physical structure remaining from the historic school is the former headmasters house.