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Particularly Special Place
Top Recommended Hiking Routes
near Wintergreen, Virginia
Wintergreen, Virginia 
Recommended Routes, Photos, & More
Difficult
Old Rag Loop
8.9 mi 14.3 km • 2,362' Up 719.92 m Up • 2,359' Down 718.89 m Down
Stanley, VA
Difficult
Whiteoak Canyon to Cedar Run Loop
8.2 mi 13.1 km • 2,255' Up 687.39 m Up • 2,255' Down 687.38 m Down
Stanley, VA
Difficult
Three Ridges Loop Trail
13.4 mi 21.6 km • 3,565' Up 1086.57 m Up • 3,564' Down 1086.44 m Down
Nellysford, VA
Intermediate/Difficult
Rose River Loop
3.8 mi 6.1 km • 796' Up 242.59 m Up • 797' Down 242.97 m Down
Stanley, VA
Intermediate/Difficult
McAfee Knob
7.4 mi 12.0 km • 1,340' Up 408.53 m Up • 1,344' Down 409.56 m Down
Salem, VA
Intermediate/Difficult
Dolly Sods Wilderness
19.6 mi 31.6 km • 1,364' Up 415.85 m Up • 1,365' Down 416.06 m Down
Davis, WV
Intermediate/Difficult
Hawksbill Mountain Loop
2.6 mi 4.2 km • 600' Up 183 m Up • 644' Down 196.36 m Down
Stanley, VA
Intermediate
Dark Hollow Falls
1.7 mi 2.7 km • 495' Up 150.91 m Up • 495' Down 151.02 m Down
Stanley, VA
Intermediate/Difficult
Bearfence Loop Trail
1.1 mi 1.8 km • 232' Up 70.77 m Up • 232' Down 70.65 m Down
Stanley, VA
Difficult
Virginia's Triple Crown Loop
34.8 mi 55.9 km • 6,774' Up 2064.63 m Up • 6,778' Down 2065.99 m Down
Salem, VA
Difficult
Humpback Rocks
1.8 mi 2.9 km • 817' Up 249.16 m Up • 817' Down 249.02 m Down
Nellysford, VA
Difficult
Little Devil Stairs Loop
5.5 mi 8.9 km • 1,453' Up 442.8 m Up • 1,429' Down 435.54 m Down
Washington, VA
Difficult
Dragon's Tooth
4.8 mi 7.7 km • 1,162' Up 354.24 m Up • 1,174' Down 357.81 m Down
New Castle, VA
Intermediate/Difficult
Piedmont Overlook Loop
5.2 mi 8.4 km • 969' Up 295.43 m Up • 973' Down 296.45 m Down
Shenand…, VA
Intermediate/Difficult
Riprap Hollow
9.7 mi 15.7 km • 1,891' Up 576.42 m Up • 1,891' Down 576.3 m Down
Crimora, VA
Intermediate/Difficult
Double Falls Loop
6.9 mi 11.0 km • 1,226' Up 373.62 m Up • 1,221' Down 372.24 m Down
Grottoes, VA
Intermediate/Difficult
Big Schloss from Wolf Gap
4.6 mi 7.3 km • 986' Up 300.44 m Up • 993' Down 302.72 m Down
Moorefield, WV
Intermediate
Upper Hawksbill Ascent
2.2 mi 3.5 km • 412' Up 125.5 m Up • 411' Down 125.2 m Down
Stanley, VA
Difficult
Rock Castle Gorge Trail
11.0 mi 17.8 km • 2,377' Up 724.46 m Up • 2,381' Down 725.82 m Down
Woolwine, VA
Intermediate
First Battle of Manassas
5.2 mi 8.3 km • 309' Up 94.19 m Up • 309' Down 94.32 m Down
Bull Run, VA
Intermediate/Difficult
Sharp Top Out-and-Back
2.9 mi 4.7 km • 1,242' Up 378.58 m Up • 1,242' Down 378.48 m Down
Buchanan, VA
Intermediate
Bull Run-Occoquan Trail
17.9 mi 28.8 km • 1,531' Up 466.79 m Up • 1,467' Down 447.06 m Down
Loch Lo…, VA
Intermediate
Blackrock Summit Loop
1.2 mi 1.9 km • 219' Up 66.62 m Up • 206' Down 62.86 m Down
Grottoes, VA
Difficult
Climbing the Priest
8.2 mi 13.1 km • 3,092' Up 942.4 m Up • 3,093' Down 942.69 m Down
Nellysford, VA
Difficult
Whiteoak Canyon - Hawksbill Summit Loop
13.6 mi 21.8 km • 3,652' Up 1113.19 m Up • 3,649' Down 1112.08 m Down
Stanley, VA
Intermediate
Compton Gap to Compton Peak
2.3 mi 3.7 km • 617' Up 187.93 m Up • 617' Down 188.17 m Down
Front R…, VA
Intermediate/Difficult
Dolly Sods Wilderness - North Day Loop
12.3 mi 19.7 km • 890' Up 271.28 m Up • 890' Down 271.31 m Down
Davis, WV
Intermediate
Turk Mountain Out and Back
2.4 mi 3.9 km • 614' Up 187.03 m Up • 613' Down 186.84 m Down
Crimora, VA
