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Top Rated Trails
near Winchester, Virginia
Winchester, Virginia 
Recommended Routes, Photos, & More
6.8
mi
10.9
km
#1Wakefield Park
Intermediate
Ravensworth, VA
|
Intermediate
|
Ravensworth, VA |
72
|
|
5.7
mi
9.2
km
#2Ten Mile Creek Trail
Easy/Intermediate
Germantown, MD
|
Easy/Intermediate
|
Germantown, MD |
48
|
|
|
1.9
mi
3.1
km
#3Loop 1
Intermediate
Lake Ridge, VA
|
Intermediate
|
Lake Ridge, VA |
36
|
|
|
2.1
mi
3.4
km
#4Tillman West
Intermediate
Bridgewater, VA
|
Intermediate
|
Bridgewater, VA |
29
|
|
|
6.4
mi
10.3
km
#5Cabin John Trail
Intermediate
Rockville, MD
|
Intermediate
|
Rockville, MD |
38
|
|
|
5.8
mi
9.3
km
#6Seneca Ridge Trail
Intermediate
Germantown, MD
|
Intermediate
|
Germantown, MD |
34
|
|
0.6
mi
1.0
km
#7Boss Trail
Intermediate/Difficult
Lorton, VA
|
Intermediate/Difficult
|
Lorton, VA |
23
|
|
|
4.5
mi
7.2
km
#8Loop 2
Intermediate
Lake Ridge, VA
|
Intermediate
|
Lake Ridge, VA |
25
|
|
|
5.9
mi
9.5
km
#9Promise Land Trail
Intermediate
Davis, WV
|
Intermediate
|
Davis, WV |
26
|
|
|
0.5
mi
0.8
km
#10Yard Sale
Intermediate
Lorton, VA
|
Intermediate
|
Lorton, VA |
22
|
|
6.5
mi
10.4
km
#11Loop 3
Difficult
Lake Ridge, VA
|
Difficult
|
Lake Ridge, VA |
22
|
|
|
152.4
mi
245.3
km
#12Great Allegheny Passage (GAP)
Easy/Intermediate
Mount Oliver, PA
|
Easy/Intermediate
|
Mount Oliver, PA |
19
|
|
|
5.4
mi
8.7
km
#13Wolf Ridge (378)
Difficult
Dayton, VA
|
Difficult
|
Dayton, VA |
20
|
|
|
3.5
mi
5.7
km
#14South Branch Loop
Intermediate
Lorton, VA
|
Intermediate
|
Lorton, VA |
23
|
|
|
191.9
mi
308.9
km
#15Chesapeake & Ohio Canal Trail
Easy/Intermediate
Cumberland, MD
|
Easy/Intermediate
|
Cumberland, MD |
24
|
|
|
1.1
mi
1.8
km
#16Brew Thru
Intermediate/Difficult
Basye, VA
|
Intermediate/Difficult
|
Basye, VA |
15
|
|
|
6.2
mi
10.0
km
#17Bull Run Occoquan Trail
Difficult
Lake Ridge, VA
|
Difficult
|
Lake Ridge, VA |
24
|
|
|
7.8
mi
12.6
km
#18Timber Ridge Trail (431)
Difficult
Franklin, WV
|
Difficult
|
Franklin, WV |
14
|
|
|
2.2
mi
3.5
km
#19Rock & Roll / NICA Race Loop
Easy/Intermediate
Berkeley Springs, WV
|
Easy/Intermediate
|
Berkeley Springs, WV |
13
|
|
2.3
mi
3.8
km
#20High Knob Trail (1024)
Very Difficult
Franklin, WV
|
Very Difficult
|
Franklin, WV |
10
|
|
|
0.6
mi
0.9
km
#21Rooster Run Trail
Intermediate
Ruckersville, VA
|
Intermediate
|
Ruckersville, VA |
11
|
|
|
1.1
mi
1.8
km
#22Puzzler
Difficult
Massanutten, VA
|
Difficult
|
Massanutten, VA |
12
|
|
|
1.8
mi
2.8
km
#23Three Saws
Intermediate
Myersville, MD
|
Intermediate
|
Myersville, MD |
8
|
|
|
4.3
mi
6.9
km
#24FS Trail #1025 ("Deathstar")
Difficult
Franklin, WV
|
Difficult
|
Franklin, WV |
11
|
|
|
2.2
mi
3.5
km
#25Special K
Difficult
Massanutten, VA
|
Difficult
|
Massanutten, VA |
11
|
|
|
1.5
mi
2.4
km
#26Mt Vernon Trails
Intermediate
Belle Haven, VA
|
Intermediate
|
Belle Haven, VA |
17
|
|
|
69.6
mi
112.0
km
#27Massanutten Trail
Very Difficult
Strasburg, VA
|
Very Difficult
|
Strasburg, VA |
5
|
|
|
3.1
mi
5.0
km
#28Sherando Park Mountain Bike Trail
Intermediate
Stephens City, VA
|
Intermediate
|
Stephens City, VA |
26
|
|
|
1.1
mi
1.8
km
#29Quarantine
Intermediate
Massanutten, VA
|
Intermediate
|
Massanutten, VA |
11
|
|
|
1.7
mi
2.8
km
#30Creamy
Difficult
Massanutten, VA
|
Difficult
|
Massanutten, VA |
11
|
