Manny,
Are you looking for any particular roads or just the IT in general? Have you looked at the David Rumsey map collection and seen the large variety of maps they have that include the Indian Territory? I look at the adjacent states as well since they typically show the areas along the borders.

I have been reading Cooper's reports which describe roads. In particular, two different letters to Hindman, one describes where pickets should be located along the Canadian River and the other describes where pickets should be located to watch the Confederate left flank before Prairie Grove. I also recall Cooper wrote to Steele and Maxey informing them of where pickets should be and what the road conditions were for the main roads.

There are, of course, many minor roads that will never appear on any of the period maps but relatively few roads that an army could move on -- especially with a supply train. Even so, the Confederates moved almost entirely on these "minor roads" to and from 2nd Cabin Creek!

Grant Foreman's books and articles in the Chronicles of Oklahoma are good sources though no one is perfect, not even Mr Foreman.