File consists of two Appleby College holiday greeting cards. One includes an inspirational message written during World War Two and the second one consists of a photograph of students leaving The Chapel.

Series consist of correspondence and greeting cards from friends and business associates, and one story written by Robertson Davies, Canadian writer, journalist and professor.

Series consist of correspondence from Appleby College to Wentworth regarding the progress of the school, Wentworth’s donation of the school bell, invitations to events, updates on Appleby alumni, educational viewpoints, and historical information. It includes typed and written letters as well as a telegraph.

File includes letters from Raymond to Appleby College Headmaster, a letter about an old photograph of Raymond with a group visiting Appleby campus, letter's about Raymond's health as well as the health of others he knew, various letters of support and congratulations to Raymond on his performance of Abraham Lincoln including a letter from President Dwight Eisenhower offering Raymond a copy of his limited edition print of his painted portrait of President Abraham Lincoln. There are also letters of application for Raymond to enter Appleby College and correspondence from Raymond to Mr. Guest, Headmaster of Appleby College.

File consists of correspondence between Wentworth Walker and the Appleby College Old Boys Association. It includes correspondence and brochures on the planned new gymnasium and swimming pool, the 1947 Building Campaign for the Memorial Building, scholarship fundraising and other Appleby College fundraising campaigns.