Henry S. Whitehead was born in Elizabeth, New Jersey, on March 5, 1882, and graduated from Harvard University in 1904 (in the same class as Franklin D. Roosevelt).[3] As a young man he led an active and worldly life in the first decade of the 20th century, playing football at Harvard University, editing a Reform democratic newspaper in Port Chester, New York, and serving as commissioner of athletics for the AAU.

He later attended Berkeley Divinity School in Middletown, Connecticut, and in 1912 he was ordained a deacon in the Episcopal Church. During 1912-1913 he worked as a clergyman in Torrington, Connecticut. From 1913 to 1917 he served as rector in Christ's Church, Middletown, Connecticut.[2] From 1918 to 1919 he was Pastor of the Children, Church of St. Mary the Virgin, New York City.[2]

He served as Archdeacon of the Virgin Islands from 1921 to 1929.[1] While there, living on the island of St. Croix, Whitehead gathered the material he was to use in his tales of the supernatural.[2] A correspondent and friend of H. P. Lovecraft, Whitehead published stories from 1924 onward in Adventure, Black Mask, Strange Tales,[3] and especially Weird Tales. In his introduction to the collection Jumbee, R. H. Barlow would later describe Whitehead as a member of "the serious Weird Tales school".[3] Many of Whitehead's stories are set on the Virgin Islands and draw on the history and folklore of the region. Several of these stories are narrated by Gerald Canevin, a New Englander living on the islands and a fictional stand-in for Whitehead.[2] Whitehead's supernatural fiction was partially modelled on the work of Edward Lucas White and William Hope Hodgson.[3] Whitehead's "The Great Circle" (1932) is a lost-race tale with sword and sorcery elements.[3]

In later life, Whitehead lived in Dunedin, Florida, as rector of the Church of the Good Shepherd and a leader of a boys' group there. H. P. Lovecraft was a particular friend as well as a correspondent of Whitehead's, visiting him at his Dunedin home for several weeks in 1931. Lovecraft recorded in his letters that he entertained the boys with readings of his stories such as "The Cats of Ulthar". Lovecraft said of Whitehead: "He has nothing of the musty cleric about him; but dresses in sports clothes, swears like a he-man on occasion, and is an utter stranger to bigotry or priggishness of any sort."

Whitehead suffered from a long-term gastric problem, but an account of his death by his assistant suggests he died from a fall or a stroke or both.[1] He died late in 1932, but few of his readers learned about this until an announcement and brief profile, by H. P. Lovecraft, appeared in the March 1933 Weird Tales, issued in Feb 1933. Whitehead was greatly mourned and missed by lovers of weird fiction at his death.[4]

R. H. Barlow collected many of Whitehead's letters, planning to publish a volume of them; but this never appeared, although Barlow did contribute the introduction to Whitehead's Jumbee and Other Uncanny Tales (1944).