Jim Bridger guided a second train over the route in September and October 1864. Major John Owen's diary is the only known recollection of this trip. It details the day to day progress and events from Red Buttes to as far north as the Stinking Water (Shoshone) River. At that point, the journal ends. Owen had established a trading post and fort in the Bitterroot River Valley in 1850, and later became the Indian Agent in the region. He was returning to Fort Owen with Bridger in the fall of 1864. At least nine trains, including the first led by Bridger on May 20, traveled over the Bridger Trail prior to this, establishing a well-worn trace traversed by hundreds of wagons and untold numbers of stock--mules, oxen, horses, and cattle.

While traveling over the route a second time, Bridger, Owen, and members of the train often stopped to improve, and in places, reroute the trail over the present day Bridger Mountains.
Bridger and Owen left Red Buttes on September 18 and arrived at Badwater Creek on the September 26. The route appears to be the same as that traveled by the other trains earlier that summer. In fact, Owen commented on "the remains of quite a number of dead oxen strewn along the road." Modification of the trail route occurred once Bridger's train started the ascent of the Bridger Mountains. The amount of work, energy expended, and rerouting of the main road are evident in Owen's diary entries between September 27 and October 9.

"Travelled 11 miles over a very rough country road generally good but found some Very steep grades obliged to double teams in two instances. . . . [28th] Laid ove[r]. . . . [29th] road today passing over a high range of hills and being very narrow on the ridge with some very steep grades & heavy pulling Mr Bridger resolved to make a detour through a Vally [sic] to the right of the ridge cutting a new road through the vally with good grass and water . . . cutting off about five miles in the days drive. Turned off the Main road about half a mile from Camp crossed the creek and moved up the vally found the ground very good generally for locating a road stoped [sic] twice in order to fill up the bed of two dry mountain streams. . . . The course of our days drive will be the location of the road in future. . . . [30th] laid over to do some grading on the New Cut off. . . . [October 1] hard pulling up the Hill. . . . camp . . . on Cotton Wood Creek a tributary of Big Horn. . . . traveled not over two Miles. . . . [2nd] light fall of Snow lay over to Work the road. . . . [3rd] Moved the wagons Some two Miles to a small opening on the Creek. . . . [4th] Cattle lost done some work on the road. . . . [5th] Done considerable Work on the road & Movd [sic] camp Some two Miles. . . . [6th] Worked the road & Moved Camp Some miles . . . to Within a few hundred yds of old road. . . . [7th] Moved Camp through the Cañon & Came out onto an open plain Done considerable work on road. traveled some Six Miles. . . . [8th] Moved some 10 miles on a rolling road & campd. . . . Men went to river [Bighorn River] for Water. . . . [9th] Done Some Work on road. . . . Moved the train which reachd [sic] the river during the Night."

It is difficult to specifically place the changes made in the route discussed by Owen from his limited description. A careful reading of the diary entries seems to indicate that, rather than keeping northwest and crossing West Bridger Creek as is depicted on the General Land Office plats ("the Main road"), Bridger may have continued up the main fork of Bridger Creek.