Wintergreen is known mainly for its ski slopes and resort facilities but did you know that it has over 30 miles of trails? The Wintergreen Nature Foundation maintains the trails and we were very impressed by how well they are maintained. They publish a map of all their trails which can be purchased from the WNF at the Trillium House.
This is actually a series of hikes that create one tough circuit with a ton of elevation change but you will be rewarded with many great overlooks and some beautiful waterfalls on the Upper Shamokin Falls trail a few miles from the end. This is the first really good circuit hike south of Shenandoah National Park. There is no camping allowed on the trail. A big thanks goes to frequent hikingupward.com reviewer BrandonB for the lead on these great trails at Wintergreen.
Some of the trails that make up the perimeter hike are closed from November to the end of March so before you go during that time period call the Wintergreen Nature Foundation (434-325-8169) for trail closings.
We began the hike at the Dripping Rock parking area on the Blue Ridge Parkway. Head North on the White-blazed A.T for about 150 yards and bear to the right on an unmarked trail (rock cairn). Stay on the trail for 0.1 miles crossing Laurel Springs Drive. On the other side of the road the yellow blazed Old Appalachian Trail begins. You will begin to see some of the Wintergreen homes to the right and left. In 0.3 miles you will pass the Upper Shamokin Gorge Trail on the left, stay on the Old A.T. which at this point becomes red-blazed. You will see and hear Stoney Creek on your left. In 0.4 miles the Nature Preserve Loop will be on your left and in another 0.3 miles you will cross Laurel Springs Drive again.
The first of many great views looking west towards Sherando and Torry Ridge will be 0.6 miles after crossing the road. Just after that first view is the Laurel Springs Drive Access Trail on the left. The next 0.7 miles will have multiple views and the Hemlock Drive Access trail on the left, stay on the Old A.T.
The next 0.5 miles is quite challenging with the Old AT ending at Cedar Road. Take a left onto Cedar Road for 0.1 miles then a right onto Devil's Knob Loop for 0.2 miles, reaching the Blue Ridge Overlook (N37 54.944 W78 57.509) & Parking area. This could be an alternate starting point if you are spending the weekend at Wintergreen. The Devil's Knob Trail (red blazes) begins at the right side of the parking lot and begins the steady descent to Fortunes Ridge. Stay on the Devil's Knob Trail for 0.4 miles to the Pond Hollow Trail intersection, bear right onto the Pond Hollow Trail, red blazed. The next intersection is in 0.4 miles on the left, Pond Hollow Crossover. Stay straight and in 0.5 miles cross over Wintergreen Drive (be very careful) walking on the side of the road for about 100 yards towards Fortunes Ridge Drive. The Fortunes Ridge Trail begins just on the other side of Fortunes Ridge Drive.
The Laurel Ridge Loop intersection is in 0.8 miles, bear to the right staying on the Fortunes Ridge Trail heading to the Three Ridges Overlook/Brimstone Trail intersection which you will reach in 0.5 miles. Bear to the right onto the Brimstone Trail (this section has many great views of Three Ridges) heading to The Plunge trail in 0.7 miles. If you have time, take The Plunge trail (yellow blazes) to see a great overlook, well worth the short side trip. If not, bear right onto the Blackrock Trail for 0.7 miles until the Blackrock Circle access trail, bear right onto the Pedlars Edge Trail. From this point on until the end of the hike there will not be very many views but hang in there because if the water is flowing, the Shamokin Falls will be worth it at the end of the Logger's Alley trail.
On the Pedlar's Edge Trail go 0.3 miles and turn onto a gravel fire road. In 0.2 miles look for a Yellow & Red Arrow sign on the left, turn left onto the trail. You will pass underneath and alongside a Power Line in 0.5 miles and then making a sharp turn to the right in 0.1 miles onto a dirt road, staying on the Pedlar's Edge Trail. Take a left in 0.1 miles continuing on the Pedlar's Edge Trail. In 0.2 miles there is one of the rare views on this part of the trail looking over to Cedar Cliffs. Just after the view and over the next 0.1 miles are a couple of intersection signs, stay on the Pedlar's Edge Trail for both of them. The third sign you come to will lead you across Stony Creek to the Hemlock Springs Trail/Hemlock Springs Loop (one tree has 3 red blazes at this crossing). Stony Creek was flowing pretty well so we had to go downstream a little to find a suitable crossing.
Soon after crossing Stony Creek you will come to the Intersection of the Hemlock Springs Loop, stay straight heading to Cedar Cliffs South. In 0.2 miles turn left onto Cedar Cliffs Main trail (there are misleading trail markings on the back of this sign which you will see first before you turn left, ignore them). Within 100' quickly turn right at the next intersection onto the Cedar Cliffs North trail. This is a very tough part of the trail ending at the Logger's Alley Trail in 1 mile. Turn right onto Logger's Alley Trail just after passing the Outdoors Ropes Course area. There was no sign to turn right as it disappeared over the winter. You will cross 3-4 of Wintergreen's ski slopes which accounts for some of the trail closings in the winter.
It is about 0.4 miles to cross all the ski slopes and then you will be on an old logging road with very few faded red blazes. Logger's Alley was our least favorite part of the trail. You will also see occasional blue 'Intermediate' signs and 1 mile after crossing the slopes you will see a red and white sign that says '1.5 Miles'. In 0.2 miles after that sign you will be rewarded with the 1st of the Upper Shamokin Falls. It was flowing well in April when we were there. After viewing the Falls return to the intersection sign just before the Falls and head up towards the Upper Shamokin Falls trail and in 0.1 miles you will be see a 2nd set of Falls, this is even better than the first. Continue up the trail heading to the Upper Shamokin Gorge trail. On the right in 0.2 miles will be the Laurel Springs Drive access trail, stay straight heading to the Shamokin Gorge trail. The Chestnut Springs Trail will be on the left in 0.1 miles, stay straight, the sign will point to Laurel Springs Gap Overlook which will be in 0.1 miles. Stay on the Upper Shamokin Gorge Trail arriving at the Old A.T. trail in 0.4 miles, turn right and cross Laurel Springs Drive in 0.3 miles reaching the A.T. intersection in 0.1 miles. Turn left to return to the Dripping Rock Parking Area.