Hiking Upward has a decent map/description of the Wintergreen perimeter trails, and I've taken this photo of the official trail map provided by the Nature Foundation at Wintergreen:
|Wintergreen Trail Map|
The perimeter trails are in red on both the map and blazes. The alternate trails are in yellow. To stay on the perimeter, there are a few road crossings and a couple short road connectors.
Getting ThereWintergreen Resort is on Route 664 1 mile south of the intersection with the Blue Ridge Parkway at Reeds Gap, and 5 miles north of Route 151 where Devils Backbone brewpub and the Ski Barn are. There's a huge green sign at the entrance. Go up Wintergreen Drive about 2.5 miles, and bear right at the fork in front of the fire station to go on Mountain Inn Loop. Take a right on Grassy Ridge Drive and take that down to the parking lot at the dome. The trailhead is nearer the gravel parking lot than the paved one. Unfortunately the trail head isn't simple to find. To head clockwise, go past Ridgely's Fun Park with the teepee and look for a small brown sign at the ends of the woods for Cedar Cliffs North. To head counter clockwise, take the gravel/dirt road across the ski runs, which becomes the Loggers Alley trail. But it's best to go with someone who's been there before anyway.
Navigation AidsThe trails change names at roads and alternate trail crossings, usually without incident. Going clockwise, from Cedar Cliffs North you have to jog left for maybe 50 yards then right to Cedar Cliffs South to stay on the red perimeter. Down at the south end, when the Fortune's Ridge Trail hits Wintergreen Drive, go down the road about 25 yards and look for the Pond Hollow trail head across the road. This takes you up a long climb to the highest point of the trails at the Blue Ridge Overlook. Take a left onto Devil's Knob Loop, and left on Cedar Drive, and look for the trailhead for the Old AT trail on the right part way down. (In the winter at the end of Cedar Drive you may be able to pick up a trail that was roughed out but not used for UROC, which comes out to 664 just below Reeds Gap where the AT crosses, but in the summer it's overgrown.) The Old AT crosses Laurel Springs Drive once but continues directly across the road. Further down the hill look for a right onto Upper Shamokin Gorge to stay on the red perimeter trails. (If you continued on the Old AT you'd cross Laurel Springs Drive once again, and shortly after that you'll run into the AT and then the Blue Ridge Parkway at Dripping Rock.) On Upper Shamokin Gorge look for a right onto Chestnut Springs to stay on the perimeter, but you might want to continue a bit further down to a waterfall and then double back. Chestnut Springs Trail comes to a T with Loggers Alley, take a right to get back to the parking lot.
Going counterclockwise, the only additional thing to watch for is a left turn to stay on the Pedlars Edge Trail, otherwise you'll wind up in Intern Gulch, so named because not one but two nature foundation interns missed that trail and would up down at a trailer on some dead end road coming out of the valley. Not recommended!
WarningsThe trails at Wintergreen are quite technical. Some of them are extremely rocky. To compound things, much of it is greenstone, which gets very slick when wet. Particularly rough trails are Blackrock, Brimstone, Pedlars Edge, Cedar Cliffs North, and Upper Shamokin Gorge. DO NOT run these when they are wet. There are a couple places where you have to slide off a rock face onto another rocky landing and it's hard enough in dry conditions.
Run with a buddy, because there are many places where you can turn an ankle or fall and hit a rock. These trails are much more technical than the AT. Drew Kreuger has the FKT of the loop, 2:53. For most of us it is a 4-5 hour trek.
There is water at various points but since there is salt run off from roads, fertilizer from the golf course, whatever they put in the water for snow making, etc, I recommend carrying what you'll need and perhaps dropping water at road crossings.
You shouldn't lose the trail, but if somehow you do and cannot back trace to find the trail, go UP, not down. Before too long you will hit one of the many roads or ski slopes on top of the mountain. If you go down, you could go many miles before finding any signs of civilization, and you could hit a cliff face that will stop you.
Alternate RunsOne of my favorite runs is to start at Loggers Alley by the dome, starting the perimeter clockwise. Continue on Loggers Alley when it turns into a yellow trail, and just after a creek crossing take a left onto Morgan's Loop, which is not on this map but runs parallel to Upper Shamokin Falls Trail. Go run at the Laurel Ridge road access trail to the road. Go uphill on the road for 1/4 mile and look for the Old AT trail head on the left. It starts as yellow and turns to red. Cross the road and continue on the Old AT and go about another mile and look for the 2nd yellow trail on the left, Hemlock Drive access. Take this yellow trail to the cul-de-sac, and take that street to a left Devils Knob Loop road and an immediate right on Wintergreen Drive. Look for a brown diamond sign giving you an alternate dirt and asphalt path to follow rather than running on the road. Where that path crosses Blue Ridge Drive, follow the Highlands Leisure Trail down to the ski village. Take a path past the big white tent back down to the parking lot. The loop is almost exactly 10K.
Add on about 3 miles by taking the gravel/dirt road out of back end the parking lot down to the Hemlock Springs Trail on the left just before you hit the big water tank. You might also see some twisty mountain bike trails to follow rather than the road. I can't describe exactly how to find or use them but they are great to explore. Anyway, stay left of the creek and Hemlock Springs Tr becomes Cedar Cliffs South. When that comes to a T, go right 100 yards or so to a fantastic rocky view overlook. Backtrack and stay straight on Cedar Cliffs Main back to the gravel road, and turn right to take that back to the parking lot.
The Laurel Ridge Loop trail, especially the south part starting with the trail head off Mountain Inn Loop is another nice route. Combine it with the Fortune's Ridge Trail and Pond Hollow up to the Pond Hollow Crossover back to the Laurel Ridge Loop trail. Going right from here is a more runnable way back than left.
There are also some mountain bike trails in and around the ski slopes that look very runnable.
The best option may be to connect to the AT. The Old AT trail crosses Laurel Springs Road and within 200 yards you are at the AT where it crosses the Blue Ridge Parkway at Dripping Rock between mile posts 9 and 10. Heading north, it's about 4 miles to Humpback Rocks and 14 miles total to Rockfish Gap/Afton. The first mile south takes you to a nice view similar to the view at the Raven's Roost overlook off the parkway. Beyond that the profile looks promising but it's extremely rocky. 5 miles to Reeds Gap total.