The mountain water sources and the low north south divide that lay between the two Doubtful canyons made it a favored shortcut for early east west travelers to the Southern Emigrant Trail wagon road that ran farther south before turning west. Doubtful Canyon and West Doubtful Canyon formed the pass where the Butterfield Overland Mail passed through the Peloncillo Mountains. Later near Steins Peak, the Steins Peak Station of the Butterfield Overland Mail was located in Doubtful Canyon. Steins Peak Station was destroyed and its keepers killed by the Apache in 1861. On May 4, 1864, soldiers of California Column fought a band of Apache in the Skirmish in Doubtful Canyon, in the canyon near Steins Peak.