Pine Mountain Trail (Pound Gap to Twin Cliffs Overlook)

Length/Type: Approximately 2.2 miles one-way, out-and-back; Difficulty: Moderate (some moderately steep but short climbs, poor footing in several stretches); Other Considerations: See parking considerations in the directions at the end of this post. A detailed trail map is available via the park’s website.

The 44-mile long Pine Mountain Trail is paradoxically one of the central Appalachians’ most scenic and underused long-distance trails. Designated a Kentucky State Park, the PMT follows its namesake, Pine Mountain, from Elkhorn City, Kentucky southwestward along the mountain’s spine all the way to US Highway 119 above Whitesburg, Kentucky. Along the way, the trail never strays far from the mountain’s spine, which also serves as the Virginia/Kentucky border for much of its length. Although just over 40 miles of singletrack trail are currently in place, plans exist to lengthen the PMT to 120 miles total, creating a linear trail corridor linking Breaks Interstate Park (at the trail’s existing northern terminus) with Cumberland Gap National Historical Park to the south.

The trail’s existing path is broken into two sections, designated with four-lane US-23 as a break point: the 28-mile Birch Knob Section is located east of the gap, with the Highland Section’s 16 miles located from US-23 west. The highway, in fact, forms a perfect starting point for dayhikes in both directions, as most of the trail’s access points outside of either end are one-lane forest roads or, more commonly, steep singletrack connector trails. Another benefit of US-23 is that decent views can be had from companion overlooks located a few miles in on either side of Pound Gap, the low point in the ridge that US-23 uses for its journey from Kentucky into Virginia.

The Hike

The Twin Cliffs Overlook forms the first destination on the PMT headed west from US-23. The western end of the trail begins in as assuming place: at the northwest end of the parking lot for the gas station and rest area built in Pound Gap itself. Beginning at a kiosk located at the margin of the woods leaving the parking lot, the yellow-green blazed PMT quickly passes a trail register (please do sign in to help the park keep track of trail usage) and slabs around the ridge a hundred yards or so to a signed junction with the blue-blazed Red Fox Trail. This route heads to the left down the south face of Pine Mountain and follows the old road route through Pound Gap – a path with a rich history including moonshining, murder, and a self-predicted resurrection – all the way to a paved spur road off of US-23 at the foot of the mountain.

From this junction, the PMT continues through a stile (built to block horse traffic) and soon begins climbing up a narrow hollow. This theme will continue, winding above the hollow and onto the crest of a spur ridge, eventually entering a linear clearing built to provide passage for a high-voltage transmission line carrying electricity over Pine Mountain from generation facilities in Kentucky to thousands of residents in southwest Virginia. A gravel access road also crosses the trail near this clearing. From here, the trail continues to slab around the ridge, generally following its contour and gaining little significant elevation, to the Jack Sautter Campsite at 1.3 miles from the trailhead at Pound Gap.

Although inconspicuous at first glance, this campsite is a key point on the Highland Section of the PMT. For the 1.3 miles leading to the campsite, the PMT is placed squarely within Wise County, Virginia, winding just below the crest of Pine Mountain on its route west. At the campsite, however, the PMT joins the summit of Pine Mountain for the first time, straddling the Kentucky and Virginia state line. The trail will generally not stray too far from the state line along much of its route until the border between Kentucky and Virginia bends south, away from the ridgecrest, several more miles to the west. A signed side trail also drops off of the ridgecrest from this campsite 0.2 miles to the Old Meade Homeplace, a historical landmark and a water source for long-distance hikers (be sure to treat any water found on the trail before use).

The main trail continues climbing past the campsite and quickly reaches a high knob on the ridgeline, where views can be had in both directions through the trees during the winter months. This knob also marks the starting point of a unique stretch of trail where the path will form a broad, near-horseshoe bend around the headwaters of Stacy Branch. The northern side of the mountain is incredibly steep here and even forms more of a precipitous cliff than simply a steep mountainside (see why in the Nature Notes section of a different hike on Pine Mountain). The trail will actually run just along the rim of this cliff a short distance, which is located entirely under the forest canopy and forms the start of a drop of nearly 1000 vertical feet to the settlement of Payne Gap, found just over only one-quarter mile away in linear distance from the ridgecrest. Few mountains in the entire Appalachian chain experience that dramatic of an elevation loss, making this section of Pine Mountain especially rugged and scenic.

The PMT beginning to wind around the ridge above Stacy Branch.

After rounding the western side of Stacy Branch’s headwater bowl, the PMT climbs again, steeply at times, and eventually rises above a small seep and seasonal stream to a series of large sandstone boulders near this tributary’s head. One more short, steep pitch up and through a notch in these boulders brings you to a low gap and a junction with the side trail to the Twin Cliffs Overlook, located around 2.2 total miles from the Pound Gap Trailhead.

Panorama from the first set of ledges at the Twin Cliffs Overlook, looking into Wise County, Virginia

The side trail turns left off of the PMT at this junction and quickly reaches a mostly flat, open rock ledge with scenic views to the south. The coalfields of Wise County, Virginia rise above the Pound River Valley to the south from this overlook, with the more forested and undisturbed summits of the Jefferson National Forest rising to over 4,000 feet above sea level in the distance. While this view is indeed scenic, most hikers fail to notice that a more distinctive view can be had to the opposite direction by following the side trail across this ledge, back into the woods, and up a steep slope to a high point of sandstone just beyond. This leads out to a much more precipitous overlook that provides views off the north side of the mountain into Kentucky and even down the narrow spine of Pine Mountain to the north and east. From here, the steep slopes of Pine Mountain fall off to the more gentle hills of the Appalachian Plateau, which extends unbroken from here to near Lexington, KY many miles distant. To return back to the cat at Pound Gap, simply retrace your steps back down the side trail to the junction with the PMT and turn right, following your original route back to the trailhead.

Looking north, down the spine of Pine Mountain, from the upper portion of Twin Cliffs

Nature Notes

Pound Gap, the starting point for this hike, is an incredibly important place in the landscape of southwest Virginia and eastern Kentucky. Serving as one of only a handful of places where roads provide vehicular access across the imposing structure of Pine Mountain, Pound Gap is notable for its large “cut,” or passage dissected into the mountain by humans that allows for the passage of US Highway 23 on its long journey from Florida to Michigan.

The reason Pound Gap is so famous today is that, in 1998, the improvement of US Highway 23 exposed a large section of rock in the gap, particularly on the western side of the ridge. This rock appears today as a layer cake of sorts, showing the sedimentary rock layers originally deposited in shallow seas hundreds of millions of years prior to the present-day Appalachians. That’s not all that makes Pound Gap special, though: this particular cut also exposes the sharply angled directions of this rock – a “thrust-fault” created when pressure from the collision of the North American and African continental plates forced these layers of rock up and over those lying adjacent and to the north and west (technical info here). This unique exposure of a key geologic feature has made Pound Gap famous in the geological world and has even led to the establishment of the cut as a Distinguished Geological Site.

Looking back into Pound Gap from the PMT.

Long before Pound Gap was widened to make way for today’s four-lane highway, though, it and similar gaps in major Appalachian ridges served as important points of travel for both wildlife and humans alike. Large, prehistoric megafauna, including mastodons, mammoths, and musk ox, used gaps such as these for migration, as did early Native American populations. Daniel Boone used the gap as a point of passage into Kentucky to warn surveyors of impending Native American attacks, and a Civil War battle even took place near the gap due to its importance in moving troops and supplies. This history even extends to more recent events, including the infamous Pound Gap Massacre. There’s perhaps not another spot in the immediate region that embodies the importance of geologic history to Appalachian life than this spot and its companion ridge traversed during this hike.

Directions: Pound Gap is located where US Highway 23 crosses the Virginia-Kentucky State Line atop Pine Mountain, located approximately 20 miles north of Norton, Virginia and 32 miles south of Pikeville, Kentucky. The Pine Mountain Trail crosses the four-lane highway in the gap. The safest parking for this hike (eliminating the need to cross US Highway 23) can be found behind the gas station on the west side of the gap, where the trail re-enters the woods. As this is private property, however, be sure to ask permission from the business owners prior to leaving a car for a dayhike.



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