In 1850 Basil B. Pleasants resigned, Thomas J. Bowie died, and William Lingan Gaither declined the position of Trustee. Each vacancy was filled and remained so for the rest of the decade. Those elected were Elisha J. Hall, B. Worthington Waters, and Enoch B. Hutton.

E. B. Prettyman was chosen as Principal in 1853 and continued on in the position through the 1850s. In 1857 he wished to resign, but the Board of Trustees refused to accept his resignation. Charles B. Young was an associate principal (1853) and assistant teachers were A. M. Sawyer (1853), William Grady (1853), Dr. C. L. Hogeboom (1856) and J. Alonzo Christman (1858). Mrs. Trippe gave up the management of the boarding house in 1855 at which time the Board thanked her for "the excellent and efficient manner in which the boarding house had been conducted by her."(11)

The Trustees found renewed support during the late 1850's. The Mutual Fire Insurance Company appropriated money (1857), the State's annual donation increased (1358) and a loan was received from Miss Sarah Holland (1858). With the money received from these sources, the Trustees pursued an enlargement of the boarding house and further improvements to the Academy (1858).

11 "Board Meeting dated March 1855," Brookeville Academy Minute Books, 2 Vols., 1822-1934, MS.149, Manuscripts Division, Maryland Historical Society Library.