John Henry and his race against a steam drill may both be real, so the song has a very specific setting in place and time. Unfortunately, historians disagree as to exactly where and when Henry's contest with the machine took place. Therefore, the song's setting can't be fixed with complete certainty.
For many years, the Big Bend Tunnel on the C&O line in West Virginia was identified as the site of the historic battle. Constructed between 1870 and 1872, the tunnel was even named in some versions of the song. However, more recent research has challenged this conclusion.
Historian Scott Reynolds Nelson has argued that railroad company records don't list any steam drills in their inventory for this project, nor would the soft shale of Big Bend Mountain require the machine. Instead, Nelson says, the race took place north and east of "Big Ben," at the Lewis Tunnel. This rocky mountain called for state-of-the-art technology, and the railroad company responded by bringing in steam drills.
Yet another scholar, John Garst has argued that other documentary evidence points to a setting further south in Alabama and a date 15 years later. Based on letters from railroad workers working for both the C&O and Columbus and Western Railways, Garst argues that John Henry's race took place in either Coosa or Oak Tunnel in either 1887 or 1888.