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File consists of records pertaining to Harward Eastman Chaffey's time at Appleby School as a student as well as his letters to Mr. Guest after he had enlisted to participate in World War 1 (one). There are also letters from Harward to his father, which were sent along to Mr. Guest.

File consists of records pertaining to Aubrey de V.A. Turquand's time at Appleby School as a student as well as his letters to Mr. Guest after he had enlisted to participate in World War 1 (one). It also includes letters after his death, a subscription list for the Turquand Tablet and information about the tablet, his application form for Appleby School and correspondence regarding fees and payment for his time at Appleby School.

File also includes a silk embroidered Christmas postcard (December 1915) from Aubrey Turquand to Mrs. Guest.

File consists of Appleby Old Boys Association newsletter, News of Appleby. These newsletters were in addition to the Argus Yearbook. The 1943 newsletter details many Old Boys and their military status during World War Two. The 1947 newsletter providing information on The Building Campaign, The memorial window in The Chapel dedicated in memory to J. William Weis. It also includes personal updates for many Old Boys.

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.