In the Shade of the Old Apple Tree is a popular song dating from 1905. It was written by Harry Williams and Egbert Van Alstyne (music). Popular recordings in 1905 were by Henry Burr; Albert Campbell; Haydn Quartet; and by Arthur Pryor's Band. Other recordings were by Duke Ellington, Louis Armstrong and The Mills Brothers and Alma Cogan (1962). Bing Crosby included the song in a medley on his album On the Sentimental Side (1962).

Henry Burr was a Canadian singer, radio performer and producer. He was born Harry Haley McClaskey and used Henry Burr as one of his many pseudonyms, in addition to Irving Gillette, Henry Gillette, Alfred Alexander, Robert Rice, Carl Ely, Harry Barr, Frank Knapp, Al King, and Shamus McClaskey. He produced more than 12,000 recordings, by his own estimate, and some of his most popular recordings included "Just a Baby's Prayer at Twilight", "Till We Meet Again" with Albert Campbell, "Beautiful Ohio", "I Wonder Who's Kissing Her Now" "When I Lost You" and "In The Shade Of The Old Apple Tree". A tenor, he performed as a soloist and in duets, trios and quartets.