The Little Dry Run Trail has the potential to be an amazing trail. The grade is generally gentle, the forest is beautiful, the trail weaves alongside and across Little Dry Run, and it is the sole trail to cut through the Little Dry Run Wilderness. The trail is also open to horseback riders and unfortunately that has led to some areas that have gotten wide and muddy with deep hoofprints to negotiate. It is their right to use and enjoy the trail just as much as anyone else, but this trail could use some trail work to repair muddy sections, reroutes, and areas where the trail has become a bog where people and horses have traversed the mud instead of going right through it which offers the least damage.
You can start from the shared trailhead with the superb trailwork of Henley Hollow Trail #306
on Hwy 21 a few miles south of Speedwell. Cross to the west side of the highway and follow the trail alongside and across the creek at times. The trail generally has a slight and gentle uphill for the first 2.5 miles. At this point, the trail starts to gain elevation as it switchbacks to a junction with the VA Highland Horse Trail. The gently-graded and doubletrack VA Highlands Horse Trail going to the left (east) will take you back to Hwy 21 a few miles south of the trailhead. Going to the right on the VA Highlands Horse Trail (west) will take you toward Hale Lake and in the general direction of Grayson Highlands. To stay on the Little Dry Run Trail continue straight. The trail looks steep uphill when viewed from this junction, but it soon mellows out.
After leveling, the trail starts to climb again before intersecting with the Iron Mountain Trail: Comers Rock Section
and the Comers Rock Overlook Trail
(worth the side jaunt!) as well as the Comer Rock Camping area. The camping area and Overlook Trailhead offer alternative trailheads at the southern end of the Little Dry Run Trail. The upper section of Little Dry Run Trail south of the VA Highlands Horse Trail does not have the horse hoof damage to the trail or mud that the lower section has, though it is steeper.
This is a shared trail with other hikers and horses. When encountering a horse, it is proper etiquette to step off the trail to the downhill side and stop until the horse has passed. Also, be sure to wear bright colors during hunting season (October 1st through the first week of January). And be friendly; say "hi" to other folks out enjoying the wilderness!