I found it odd that a 50th Tenn. soldier be at Holly Springs on that date. At this time both armies were not doing much in this sector of the war, the fighting around Corinth was from Oct.3-12, and Grants Central Railroad campaign would not start until Oct. 31, 1862. So at this time both armies were busy exchanging prisoners. A great deal of prisoners from Fort Donelson and Henry were part of this exchange period. It apparently was done in groups of prisoners, probably associated with where they were held in the North.
Around and on the date you specified I fould a lot of message traffic between General Gregg (who would later command Gregg's Brigade including the 50th Tenn. at Vicksburg in late Dec. 1862 and later Port Hudson in early January 1863), General Van Dorn, and General Price.
Many prisoners were sent from Guntown to Meridian. Others were sent to Jackson and later to Vicksburg. Some were sent by Union authorities at Baldwyn, Mississippi, south, and I also found....
Offical Record, Series 2, Volume 4, Pages 924 to 938
"Jackson, Miss., October 26, 1862.
Maj. J. H. WADDY, Assistant Adjutant-General.
MAJOR: I have learned from prisoners arriving here that General Van Dorn has ordered the prisoners paroled by the Federal authorities at Bolivar [Tenn.] and returned thence to Holly Springs to remain at that place quartered with their regiments. If it is desired that these prisoners shall report to me it will be necessary for General Pemberton to issue an order requiring it. The prisoners at Holly Springs so far as I can learn are not accounted for at these headquarters and we can obtain
a list of them only by their reporting.
This would indicate that some of these prisoners came through Holly Springs, Miss.