Outdoors · Winchester
Share Winchester, VA parks, trails & bike paths
About 9.9% of Winchester is conserved land, roughly 581 acres. There are about 7.8 miles of mapped trails, and the biggest networks are in Kernstown Battlefield Park (1.7 mi).
Conserved land, trails, parks and bike routes in Winchester, measured from OpenStreetMap and USGS data.
At a glance
Share Winchester outdoors
Conserved land
9.9%
581 of 5,867 acres
Trails
7.8 mi
0.8 mi per sq mi · 6 on conserved land
Parks & preserves
11
21 conserved acres per 1,000 residents
Bike routes
4.5 mi
0.0 mi lanes · 4.5 mi off-road paths
Conserved land is a share of the whole town area. Bike lanes are often missing from the map in smaller towns, so that number is likely low.
Map
Conserved land, trails & bike routes
Conservation land Easements (mostly private) Trails Bike routes Things to do
🏊 Kids Pool 🏊 Unnamed public pool 🏊 Unnamed public pool in Jim Barnett Park 🛝 Daniel Morgan Intermediate School Playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground in Park Place 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground in Whittier Park 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground 🛝 Unnamed playground in Jim Barnett Park 🛝 Unnamed playground in Jim Barnett Park 🛝 Unnamed playground in Frederick Douglass Park 🛝 Unnamed playground in NESW Park 🛝 Unnamed playground 🛝 Unnamed playground in Jim Barnett Park 🛝 Unnamed playground ⛰️ Bowers Hill 🧺 Unnamed picnic area 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🧺 Unnamed picnic area in Jim Barnett Park 🌱 Unnamed community garden in Timbrook Park 1 2 3 4
Show all of Winchester
Places to walk
Parks & preserves with trails
Ranked by mapped trail miles. Directions go to the nearest marked trailhead or public parking.
1 Kernstown Battlefield Park Park
54 acres1.7 mi of trail
🐕 Dog rules not recorded
166 acres0.3 mi of trail
🐕 Dog rules not recorded
3 Frederick Douglass Park Park
5 acres0.3 mi of trail
🐕 Dog rules not recorded
No trailhead mapped yet Show on map
7 acres
🐕 Dog rules not recorded
No trailhead mapped yet Show on map
All 11 parks & preserves
Showing 1–10 of 11 parks & preserves
🌳 Kernstown Battlefield Park 54 acres · 1.7 mi of trail
🌳 Jim Barnett Park 166 acres · 0.3 mi of trail
🌳 Frederick Douglass Park 5 acres · 0.3 mi of trail
🌳 Overlook 5 acres · 0.2 mi of trail
🌳 Park Place 5 acres · Winchester Parks and Rec Department
🌳 Harvest Ridge Park 2 acres · Winchester Parks and Rec Department
🌳 Rolling Hills Green Space 2 acres · Winchester Parks and Rec Department
Things to do
Beaches, playgrounds, falls & more
Pick a kind of place for the list, directions, or pins on the map above.
Playgrounds in Winchester Show all on map
Showing 1–10 of 24 playgrounds
🛝 Daniel Morgan Intermediate School Playground
🛝 Unnamed playground in Park Place
Trails
Named trails
Unpaved 6.3 mi
Sycamore Trail 0.6 mi Meadow Trail 0.4 mi Pasture Trail 0.3 mi Shawnee Springs Trail 0.3 mi Forest Loop Trail 0.3 mi Ridge Trail 0.3 mi Valley Trail 0.2 mi
Water
Lakes & rivers
Tap a name for directions.
Who protects the land
581 conserved acres
Who manages it, from PAD-US. Approximate, because parcels can overlap.
Land trusts & nonprofits
326 ac
Conserved doesn't always mean open to visitors. 2 acres are conservation easements, which are usually private land. The places listed above are parks and preserves people visit.
Biking & sports
Bike routes, courts & fields
Painted or protected bike lanes 0.0 mi
Off-road bike paths 4.5 mi
Shoulders & shared lanes 0.0 mi
Courts & fields Tennis 12 Soccer 12 Basketball 10 Baseball 8 Pickleball 6 Football 3 Skate park 1
Counts include school and college facilities, which aren't always open to the public.
Public lands
The biggest protected places in Winchester
From USGS PAD-US: who manages each one and whether visitors are welcome.
Private Conservation 538 ac Local Park 505 ac Other Easement 114 ac Conservation Easement 1 ac
Showing 1–10 of 15 places
Place Managed by Acres Public access
Glen Burnie Private Conservation Not recorded 424 Closed Jim Barnett Park Local Park Town or city 334 Open KBA Holding Private Conservation Land trusts & nonprofits 114 Restricted Abrams Creek Wetland Preserve Local Park Not recorded 50 Open Shawnee Springs Preserve Local Park Not recorded 21 Open Friendship Park Local Park Town or city 21 Open Frederick Douglass Park Local Park Not recorded 18 Open Whittier Park Local Park Not recorded 13 Open Weaver Park Local Park Town or city 13 Open Park Place Local Park Town or city 10 Open
History
Historic places to visit
Showing 1–10 of 14 places
🏛️ Judge John Handley Memorial Memorial
🏛️ Old Town Spring Building
🏛️ POW-MIA Memorial In Jim Barnett Park · Memorial
🏛️ Patsy Cline House Building
🏛️ Pritchard House In Kernstown Battlefield Park · Building
🏛️ Timbrook Park In Timbrook Park · Plaque
🏛️ Tomb of Lord Fairfax Tomb
🏛️ Winchester Historic District District
🪦 Mount Hebron Cemetery Cemetery
Trail talk
Conditions & tips from neighbors
No recent posts about Winchester's trails yet. Muddy, icy, a bridge out, where to park: a quick post helps the next person.
Sources: trails, parks, preserves, courts and bike lanes © OpenStreetMap contributors (ODbL), map data as of 2026-09-28. Conserved land: USGS Gap Analysis Project, Protected Areas Database of the United States (PAD-US) . Measured against the Census town boundary.
How we measure "Trails" are OpenStreetMap paths, bridleways, public tracks and unpaved footways, plus footways inside a park or preserve or on a named trail route. Sidewalks are left out. Areas are counted on a 20-meter grid, so overlapping parcels count once. "Conserved" includes conservation easements, which protect land from development but are usually private property. Trailheads are the nearest marked trailhead, public parking lot or information board within about 150 meters of a preserve. Dog rules come from OpenStreetMap when someone has tagged them; otherwise we show what's typical for the land manager, or say the rules aren't recorded.
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