[1][2] The order was founded in 1889 by Robert Worth Bingham, Shepard Bryan, William W. Davies, Edward Wray Martin, and Andrew Henry Patterson, who were University of North Carolina at Chapel Hill (UNC) students at the time.

Retellings of the legend vary from that point, variously stating that Miss Fanny either died of sorrow after visiting his grave every night or held his head in her arms as he passed.

In reality, it is believed that Dromgoole left for Europe after failing his entry exams or joining the Army, possibly under the name of his roommate, John Buxton Williams.

Club founder Edward Wray Martin was noted as the most vocal proponent of the castle: former UNC English Professor Charles Phillips Russell recalled, "Gimghoul Castle, medieval in form and mysterious in air, owes its existence to the romantic fancies of law student Edward Wray Martin of the class of 1891, a devoted reader of Arthurian and other medieval legends, who saw shining knights where others saw grey professors.

Martin dreamed of the club having a "great gloomy pile standing on the edge of a cliff" where it could perform secret activities.

According to Russell, the castle was finished in 1926—its elaborate stone construction the handiwork of Waldensian stone-masons from Valdese, North Carolina.

[13] According to real estate records, the 2.15-acre (0.87 ha) site is owned by a non-profit corporation the Order of the Gimghoul and has a taxable value of over $1 million.