The Old Military Road Trail starts along Holson Valley Road and connects with the Ouachita National Recreation Trail on the south side of Winding Stair Mountain. These two trails, along with the Boardstand Trail, can be combined to form a looped hike of about 23 miles. The trails travel through the western end of Holson Valley and the Indian Nations National Scenic and Wildlife Area. The Old Military Road Trail partially follows the road that was built by the military in 1832 between Fort Smith, AR and Fort Towson, OK. Many features of the original Military Road can still be seen from the trail just north of the picnic area. This old road also provided access to settlers in the area and wagon trains headed west. This is a more difficult trail where it climbs Winding Stair Mountain. The Boardstand and Old Military Road Trail are marked with white rectangles; blue rectangles mark the Ouachita National Recreation Trail. Site Amenities include accessible picnicking, picnic shelter, vault toilet, and national historic site at Old Military Road Picnic Area.

From US Hwy. 271, either take Oklahoma Hwy. I for 1/4 mile east to the Old Military Picnic Area, or take Holson Valley Road 3 miles from US Hwy. 271 to trailhead.

The trail travels through the western end of Holson Valley and the Indian Nations National Scenic and Wildlife Area. Many features of the original Military Road can still be seen from the trail.