Hiking trails near Winchester, Virginia

113 official trails lie within 25 miles of Winchester — 381 miles in total, 68 rated easy and 16 hard or expert. Every distance and elevation figure below is computed from the agency centerline and a 10 m elevation model, not crowd-sourced.

The biggest climb nearby gains 1,827 ft; the median trail gains 214 ft.

Open the map on Winchester

24 trails worth the drive

Trail	Miles	Climb	Difficulty	Drive from town
Dickey Ridge Trail	25.0	1,827 ft	Expert	37 min · 26 mi
Appalachian National Scenic Trail	16.1	633 ft	Expert	26 min · 17 mi
Tuscarora Trail	13.4	1,181 ft	Expert	35 min · 24 mi
Loudoun County Trails	12.2	110 ft	Expert	50 min · 28 mi
Tuscarora - Little N. Mountain	8.0	1,266 ft	Expert	52 min · 32 mi
Royal Shenandoah Greenway	12.4	214 ft	Expert	36 min · 25 mi
Potomac Heritage National Scenic Trail	23.0	472 ft	Hard	43 min · 27 mi
Buzzard Rock Trail	3.8	1,326 ft	Hard	39 min · 26 mi
Tuscarora - Bear Wallow	4.2	1,161 ft	Hard	44 min · 28 mi
Sherman Gap	3.3	1,251 ft	Moderate	45 min · 29 mi
Winchester Green Circle	12.8	91 ft	Hard	6 min · 2 mi
Hickerson Hollow Trail	3.5	692 ft	Moderate	58 min · 35 mi
Shawl Gap	2.3	991 ft	Moderate	47 min · 30 mi
Ted Lake Trail	2.2	1,017 ft	Moderate	42 min · 25 mi
Mud Hole Gap	4.3	471 ft	Moderate	44 min · 28 mi
The Andreae Family Wellness and Recreation Trail	2.9	406 ft	Moderate	37 min · 21 mi
Chipmunk Trail	1.6	712 ft	Moderate	44 min · 20 mi
Tuscarora - Veach Gap	1.6	962 ft	Moderate	54 min · 33 mi
Fox Hollow Trail	3.3	261 ft	Moderate	48 min · 30 mi
Vances Cove	3.5	542 ft	Moderate	23 mi (straight-line)
Tuscarora Trail (Slickee Blur)	1.4	893 ft	Moderate	44 min · 21 mi
Old Romney Grade Jeep Trail	4.3	426 ft	Moderate	37 min · 23 mi
Dickey Ridge Horse Trail	1.9	453 ft	Moderate	58 min · 35 mi
Tuscarora - Doll Ridge	3.4	244 ft	Moderate	38 min · 22 mi

Quick picks near Winchester

Easy and short: Old Mailpath Trail — 1.2 mi, rated easy, 25 mi from town
Biggest climb: Dickey Ridge Trail — 1,827 ft over 25.0 mi, 18 mi from town
Longest: Dickey Ridge Trail — 25.0 mi, 18 mi from town

What the trails reach

Summits: Dickey Ridge Trail to Dickey Hill; Appalachian National Scenic Trail to Buzzard Hill; Tuscarora Trail to Eagle Rock; Buzzard Rock Trail to Buzzard Rock

Lakes: Potomac Heritage National Scenic Trail to Tippecanoe Lake

Viewpoints: Dickey Ridge Trail to Shenandoah Valley Overlook; Appalachian National Scenic Trail to Bear's Den Overlook; Potomac Heritage National Scenic Trail to Luck Stone Quarry Overlook

Mountain passes: Dickey Ridge Trail to Lands Run Gap; Tuscarora Trail to Dry Gap; Tuscarora - Little N. Mountain to Fetzer Gap; Buzzard Rock Trail to Shawl Gap

Springs: Winchester Green Circle to Old Town Spring

Trail guides near Winchester

Tuscarora-Overall Run Trail — 13.8 mi, 2,445 ft climb · 29 mi away
Knob Mtn Trail — 22.2 mi, 1,816 ft climb · 29 mi away
Massanutten — 69.7 mi, 2,059 ft climb · 32 mi away
Mill Mountain Trail — 5.3 mi, 1,036 ft climb · 32 mi away
Neighbor Mtn Trail — 16.1 mi, 1,791 ft climb · 33 mi away
Hull School Trail — 12.9 mi, 1,205 ft climb · 33 mi away
Appalachian National Scenic Trail — 125.9 mi, 1,861 ft climb · 39 mi away
Nicholson Hollow Trail — 11.4 mi, 2,177 ft climb · 40 mi away

Nearby towns: Woodstock (28 mi) · Leesburg (33 mi) · Hagerstown (40 mi) · Frederick (45 mi)

All Virginia trail guides · Hiking by city · Dispersed camping rules