Headlam was the fifth son of Edward Headlam (1824–1882) and his wife Mary Anne Johnson Sowerby. He had four older brothers and a sister. His father was the fifth of seven sons of Rev. John Headlam and his wife Maria Wilson-Morley.
Headlam was educated at Rugby School, then won a demyship at Magdalen College, Oxford. He travelled extensively and wrote travel books and histories, and edited anthologies including a collection of the poems of his brother Walter.
His recreations included cricket, fishing, golf, climbing, and gardening.
In 1913, Headlam married Mary May Elles Fraser.
Works
The Story of Nuremberg. Dent. 1899.
Peter Vischer. Bell. 1901.
The Marriage of Mr. Molyneux. Hurst & Blackett. 1901.
↑Sladen, Douglas Brooke Wheelton; Lawson, William John; Oakes, Charles Henry; Addison, H. R (1913). Who's Who (65thed.). London: Adam & Charles Black. p.961 – via HathiTrust.