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Best trails in Winchester

405 Reviews
Looking for a great trail near Winchester, Virginia? AllTrails has 7 great hiking trails, dogs leash trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Sky Meadows State Park or Washington Monument State Park, we've got you covered. You'll also find some great local park options, like Bear's Den Park or Antietam National Battlefield. Just looking to take a quick stroll? We've got 5 easy trails in Winchester ranging from 1.3 to 40.2 miles and from 649 to 1,043 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Winchester
Top trails (7)
#1 - Tuscarora Trail: Biby Trail to Pinnacle Shelter
Winchester, Virginia
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(134)
Length: 5.6 mi • Est. 1 h 55 m
This out and back trail features a small loop at the end around the Pinnacle Shelter area. The trail begins at the Biby Trail head parking area atop the Shawneeland Community. The Biby Trail (white) bShow more
#2 - Third Battle of Winchester Trail
Third Battle of Winchester Battlefield Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(189)
Length: 3.5 mi • Est. 1 h 32 m
Third Battle of Winchester Trail is a 3.5 mile moderately trafficked loop trail located near Winchester, Virginia that offers scenic views and is good for all skill levels. The trail offers a number oShow more
#3 - Rose Hill Park
Rose Hill Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(26)
Length: 1.3 mi • Est. 35 m
Rose Hill Park is a 1.3 mile lightly trafficked loop trail located near Winchester, Virginia that features a great forest setting and is good for all skill levels. The trail is primarily used for hikiShow more
#4 - Winchester Green Circle Trail
Winchester Recreation Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(33)
Length: 12.5 mi • Est. 5 h 21 m
The Winchester Green Circle trail is not quite finished to its final design, but it can be walked or biked in its current state. The best place to start is near Wilkins Lake a.k.a. "the Duck Pond" atShow more
#5 - Tuscarora Trail: Biby Trailhead to Route 50
Winchester, Virginia
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(3)
Length: 8.8 mi • Est. 3 h 32 m
This is a point to point hike on the Tuscarora Trail. From the Biby Trailhead/parking area at the top of North Mountain, descend 0.7 miles through switchbacks to the Tuscarora Trail (TT) - there is a Show more
#6 - Winchester - Warrenton Scenic Drive
Winchester, Virginia
easyYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarGray Star(5)
Length: 40.2 mi
Please note: this is a scenic driving route.Show more
#7 - Jim Barnett Loop Trail
Winchester Recreation Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(13)
Length: 1.8 mi • Est. 43 m
This is a short loop that uses the Green Circle trail and the Jim Barnett Park trails. Start anywhere near the Wilkins Duck Pond and make your way north along the paved trails to the War Memorial BuilShow more