1
Middlesex Fells Reservation
Nature preserve
304 acres9 mi of trail
Reservoir TrailCranberry Pond PathSkyline TrailWillow Spring PathWyman Path
Dog rules not recorded
DirectionsTo the parking lot
Outdoors · Winchester
Winchester, MA parks, trails & bike paths
About 19% of Winchester is conserved land, roughly 767 acres. There are about 21 miles of mapped trails, and the biggest networks are in Middlesex Fells Reservation (9 mi), Brooks Parkhurst Town Forest (1.5 mi), and Sucker Brook Conservation Area (0.6 mi).
Conserved land, trails, parks and bike routes in Winchester, measured from OpenStreetMap and USGS data.
At a glance
Winchester outdoors
Conserved land
19%
767 of 4,038 acres
Trails
21 mi
3.3 mi per sq mi · 19 on conserved land
Parks & preserves
30
33 conserved acres per 1,000 residents
Bike routes
6.5 mi
1.4 mi lanes · 2.3 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
Tap a number or a place below to zoom in© OpenStreetMap contributors · USGS PAD-US
Places to walk
Parks & preserves with trails
Ranked by mapped trail miles. Directions go to the nearest marked trailhead or public parking.
2
Brooks Parkhurst Town Forest
Nature preserve
28 acres1.5 mi of trail
Loop Trail
Dog rules not recorded
No trailhead mapped yet
3
Sucker Brook Conservation Area
Managed by Town of Winchester Conservation Commission
13 acres0.6 mi of trail
Dog rules not recorded
No trailhead mapped yet
4
Locke Farm Conservation Area
Nature preserve
10 acres0.4 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
5
Mystic Lakes State Park
Nature preserve
34 acres0.3 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
6
Mount Pisgah
Managed by Town of Winchester Water Department
10 acres0.3 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
7
Smith Pond Conservation Area
Managed by Town of Winchester Conservation Commission
6 acres0.3 mi of trail
Dog rules not recorded
No trailhead mapped yet
All 30 parks & preserves
Showing 1–10 of 30 parks & preserves
Middlesex Fells Reservation304 acres · 9 mi of trail
Brooks Parkhurst Town Forest28 acres · 1.5 mi of trail
Sucker Brook Conservation Area13 acres · 0.6 mi of trail · Town of Winchester Conservation Commission
Locke Farm Conservation Area10 acres · 0.4 mi of trail
Mystic Lakes State Park34 acres · 0.3 mi of trail
Mount Pisgah10 acres · 0.3 mi of trail · Town of Winchester Water Department
Smith Pond Conservation Area6 acres · 0.3 mi of trail · Town of Winchester Conservation Commission
Winning Farm Conservation Area28 acres · 0.2 mi of trail
Leonard Field13 acres · 0.2 mi of trail
Bellino Park1 acres · 0.2 mi of trail
Who protects the land
767 conserved acres
Who manages it, from PAD-US. Approximate, because parcels can overlap.
Conserved doesn't always mean open to visitors. 5 acres are conservation easements, which are usually private land. Public access isn't recorded for 8 of 60 parcels. The places listed above are parks and preserves people visit.
Biking & sports
Bike routes, courts & fields
- Painted or protected bike lanes1.4 mi
- Off-road bike paths2.3 mi
- Shoulders & shared lanes2.8 mi
- Mountain Bike Loop (bike route)2 mi
Courts & fields
- Tennis28
- Soccer15
- Baseball15
- Basketball11
- Pickleball4
- Tracks4
- Football2
Counts include school and college facilities, which aren't always open to the public.
Nearby
Winchester and its neighbors
Towns whose outdoors data has been built so far.
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.