Middlesex Fells Reservation
Nature preserve
304 acres9 mi of trail
Reservoir TrailCranberry Pond PathSkyline TrailWillow Spring Path+1
Dog rules not recorded
Directionsto the parking lot
Capt. Josiah Locke House · Photo: User:Magicpiano · CC BY-SA 4.0A+Outdoors
Outdoors in Winchester
20% of Winchester’s land is conserved, and virtually every resident lives within a half mile of a park
Virtually every resident lives within a half mile of a park. 21 miles of mapped trail cross Winchester, 3.5 per square mile of land. 20% of Winchester’s land is conserved, about 767 acres.
Ahead of 98% of U.S. towns · #108 of 283 in Massachusetts. What drives it
Conserved land
20%
767 acres · of 6.0 sq mi of land
Trails
21 mi
3.5 per sq mi of land
Park land
511 ac
22 acres per 1,000 residents
Near a park
99%+
of residents within ½ mile
Bike routes
6.5 mi
1.4 mi lanes · 2.3 mi paths
Highest peak
344 ft
Mount Pisgah
Lakes & rivers
8
1 beach
What kind of outdoors town is Winchester?
Read from the map. The page puts what stands out first.
Land that stays wild20% of the land is conserved; a typical Massachusetts town, 21%.A trail town3.5 miles of mapped trail per square mile of land, more than 98% of U.S. towns.Parks close to homeVirtually every resident lives within a half mile of a park.History along the way67 places on the National Register.
Outdoors grade
How much outdoors does Winchester have?
On conserved land, trails, park land and how close residents live to a park, Winchester is ahead of 98% of U.S. towns, #108 of 283 in Massachusetts. All four inputs are above most U.S. towns; trail miles rank highest, park acres per resident lowest.
A+
OutdoorsA character grade: shown, never part of Winchester’s overall grade.
Conserved land20% of the land · typical MA town 21% · U.S. 4%ATrails3.5 miles of mapped trail per square mile of land (21 mi) · MA 1.9 · U.S. 0.4A+Park land22 acres of park per 1,000 residents (511 acres) · MA 91 · U.S. 13B+Parks close to homeVirtually all residents within a half mile of a park · MA 93% · U.S. 72%A+
All U.S. towns we grade (21,298)Ahead of 98%
LessMore
Massachusetts towns of 2,500+ (283)Ahead of 62%
Massachusetts towns conserve more land than most (a typical one, 21%; the U.S., 4%), so Winchester’s 20% is ahead of 44% of Massachusetts towns, while its trails per square mile lead 82% of them.
How sure. Graded on any three of the four inputs instead, the letter would range from A to A+. Trails and many small parks come from OpenStreetMap, mapped by volunteers, so coverage varies from town to town; the half mile is a straight line from each census block, so a river or highway in the way isn’t counted against it.
PAD-US, OpenStreetMap (© OpenStreetMap contributors), Census 2025 Gazetteer and 2020 blocks; details in Sources below. How TownRatings grades the outdoors →
The map
Conserved land, trails & bike routes
Tap a number to zoom to a park. Tap a layer to hide it.
Easements protect land from building but are usually private.© OpenStreetMap contributors · USGS PAD-US
Places to walk
Pick a walk
The longest trail network is Middlesex Fells Reservation, with 9 miles. Directions go to the nearest trailhead or public parking.
Brooks Parkhurst Town Forest
Nature preserve
28 acres1.5 mi of trail
Loop Trail
Dog rules not recorded
No trailhead mapped yet
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
Locke Farm Conservation Area
Nature preserve
10 acres0.4 mi of trail
Dog rules not recorded
Directionsto the parking lot
Mystic Lakes State Park
Nature preserve
34 acres0.3 mi of trail
Dog rules not recorded
Directionsto the parking lot
Mount Pisgah
Managed by Town of Winchester Water Department
10 acres0.3 mi of trail
Dog rules not recorded
Directionsto the parking lot
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
Middlesex Fells Reservation304 acres · 9 mi of trail
DirectionsBrooks 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
DirectionsMystic Lakes State Park34 acres · 0.3 mi of trail
DirectionsMount Pisgah10 acres · 0.3 mi of trail · Town of Winchester Water Department
DirectionsSmith Pond Conservation Area6 acres · 0.3 mi of trail · Town of Winchester Conservation Commission
Winning Farm Conservation Area28 acres · 0.2 mi of trail
DirectionsLeonard Field13 acres · 0.2 mi of trail
DirectionsBellino Park1 acres · 0.2 mi of trail
DirectionsGinn Field7 acres · 0.1 mi of trail
DirectionsMystic River Reservation3 acres · 0.1 mi of trail
DirectionsTown Common1 acres · 0.1 mi of trail
DirectionsChefalo Park1 acres · 0.1 mi of trail
DirectionsMystic Valley Parkway15 acres
DirectionsWell Field11 acres
DirectionsDavidson Park10 acres
DirectionsMullen Field9 acres
DirectionsManchester Field9 acres
DirectionsSachem Swamp Conservation Area8 acres
West Side Field7 acres
DirectionsPalmer Playground5 acres
McDonald Field5 acres
The Gables Cr4 acres
DirectionsHighland Park2 acres
Glen Green2 acres
Dennett Park2 acres
Elliot Park2 acres
DirectionsHorn Pond Conservation Area1 acres
DirectionsMiddlesex Park1 acres
Who protects it
767 conserved acres
20% of Winchester’s land. Who manages Winchester’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.
Town or city137 ac
Land trusts & nonprofits4 ac
State parks3 ac
Not recorded629 ac
State Park · 263 acPrivate Other or Unknown · 124 acLocal Other or Unknown · 80 acLocal Historic or Cultural Area · 74 acLocal Park · 49 ac
Good to know
Conserved doesn’t always mean open to visitors. 5 acres are conservation easements, usually private land. Public access isn’t recorded for 8 of 60 parcels. The walks above are places people visit.
The biggest protected parcels
| Parcel (PAD-US) | Managed by | Acres | Public access |
|---|---|---|---|
| Middlesex Fells Reservation State Park | Not recorded | 263 | Open |
| Winchester Country Club Private Other or Unknown | Not recorded | 119 | Restricted |
| Wildwood Cemetery Local Historic or Cultural Area | Not recorded | 73 | Open |
| Mystic Lakes State Other or Unknown | Not recorded | 43 | Open |
| Town Forest Local Resource Management Area | Town or city | 28 | Open |
| Calvary Cemetery Private Historic or Cultural | Not recorded | 22 | Open |
| Senior High School Athletic Fields Research or Educational Area | Not recorded | 16 | Open |
| Vinson-Owen Science Park Local Park | Town or city | 15 | Restricted |
| Sucker Brook Conservation Area Local Other or Unknown | Not recorded | 13 | Open |
| Leonard Field and Beach Local Other or Unknown | Town or city | 13 | Open |
5 smaller protected places aren’t shown.
Things to do
24 places to go in Winchester
Beaches, playgrounds, peaks, falls and more. Pick a kind.
Beaches in Winchester
Borggaard BeachIn Palmer Playground
DirectionsPlaygrounds in Winchester
Stone Family PlaygroundIn Ginn Field
DirectionsPlus 16 playgrounds without a name on the map. Tap “Show all on map” to see them.
Scenic views in Winchester
2 scenic views without a name on the map.
Peaks in Winchester
Mount Pisgah344 ft elevation · In Mount Pisgah
DirectionsGrinding Rock Hill210 ft elevation
DirectionsAndrews Hill194 ft elevation
DirectionsCommunity gardens in Winchester
1 community garden without a name on the map. Tap “Show all on map” to see it.
Trails & water
15 named trails and 8 lakes & rivers
Named trails
Open to bikes · 6.8 miUnpaved · 6.5 mi
Reservoir Trail1.4 mi
Loop Trail0.7 mi
Cranberry Pond Path0.6 mi
Skyline Trail0.3 mi
Willow Spring Path0.3 mi
Wyman Path0.2 mi
Chrysanthemum Path0.2 mi
Lightning Tree Window Path0.2 mi
Winding Path0.2 mi
Conservation Trail (green)0.2 mi
5 more trails
Granite Path
0.1 miSylvan Path
0.1 miDianthus Path
0.1 miHesprus Path
0.1 miHolly Path
0.1 miLakes & rivers tap for directions
Biking & sports
6.5 miles of bike routes
Bike lanes are often missing from the map in smaller towns, so that number is likely low.
1.4 mi
painted or protected bike lanes
2.3 mi
off-road bike paths
2.8 mi
shoulders & shared lanes
Mountain Bike LoopBike route
2 miCourts & fields
28Tennis
15Soccer
15Baseball
11Basketball
4Pickleball
4Tracks
2Football
1Skate park
Includes school and college facilities, which aren’t always open to the public.
History along the way
History →67 places on the National Register
The country’s official list of places worth saving (National Park Service). The map also marks 5 historic points from OpenStreetMap: plaques, memorials and old buildings.
Capt. Josiah Locke HouseBuilding · listed 1979
About itWinchester Savings BankBuilding · listed 1979
About itSanborn HouseBuilding · listed 1981
About itWright, Philemon/Asa Locke FarmBuilding · listed 1983
About itWinchester Town HallBuilding · listed 1983
About itHouse at 114 Marble StreetBuilding · listed 1984
About itWinchester Center Historic DistrictDistrict · listed 1986
About itUS Post Office-Winchester MainBuilding · listed 1987
About itAbijah Thompson HouseBuilding · listed 1989
About itAlbert Ayer HouseBuilding · listed 1989
About itAlfred Vinton HouseBuilding · listed 1989
About itAmy B. Mitchell HouseBuilding · listed 1989
About it55 more on the History page.
When to get out
The best walking months in Winchester: May to September
NOAA’s 1991–2020 normals for the town and the daylight at its latitude. Outlined months have long days, highs of 59 to 86 °F and little rain for the place.
| Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Daylight (h) | 9.4 | 10.5 | 11.8 | 13.3 | 14.6 | 15.3 | 15.0 | 13.9 | 12.4 | 11.0 | 9.7 | 9.1 |
| High (°F) | 36 | 39 | 46 | 58 | 68 | 77 | 83 | 82 | 74 | 62 | 52 | 42 |
| Rain (in) | 3.6 | 3.4 | 4.4 | 4.1 | 3.6 | 4.2 | 3.6 | 3.6 | 3.8 | 4.6 | 3.9 | 4.6 |
February is the driest month (3.4 in) and July the warmest (highs of 83 °F). 4.6 inches fall in October, the wettest month. The climate in Winchester →
Next door
Winchester and its neighbors
Tap a town to see its outdoors.
Questions about parks and trails in Winchester
Where can I hike in Winchester?
The longest trail networks: Middlesex Fells Reservation, 9 miles; Brooks Parkhurst Town Forest, 1.5 miles; Sucker Brook Conservation Area, 0.6 miles; Locke Farm Conservation Area, 0.4 miles. Each one is on the map above, with directions to the nearest trailhead or parking.
How much of Winchester is conserved land?
20% of its land, against a typical 21% for a Massachusetts town and 4% nationally (PAD-US). Conserved doesn’t always mean open to visitors: easements are usually private land.
Are dogs allowed on Winchester’s trails?
Middlesex Fells Reservation and Brooks Parkhurst Town Forest don’t have dog rules recorded on the map; check the signs at the trailhead.
Where can I bike in Winchester?
6.5 miles of bike routes are on the map: 1.4 of painted or protected lanes, 2.3 of off-road paths and 2.8 of shoulders and shared lanes. Named routes: Mountain Bike Loop.
Is there public land near Winchester?
35,731 acres of parks and open public land lie inside Winchester or within 10 miles of it (PAD-US), 514 of them inside the town line.
How much outdoors does Winchester have?
Ahead of 98% of U.S. towns on the Outdoors grade, #108 of 283 in Massachusetts. The grade combines the share of land that is conserved, miles of mapped trail per square mile of land, park acres per 1,000 residents and the share of residents within a half mile of a park. It’s a character grade, so it isn’t part of the overall grade. How it works.
Trail talk
Conditions, parking and favorite walks from Winchester neighbors.
Share a tip
Sources
Where this page comes from
Conserved and public land: USGS Protected Areas Database of the United States (PAD-US), service updated July 2026. Parks, trails, playgrounds, beaches and other places: OpenStreetMap (© OpenStreetMap contributors, ODbL), map data as of 2026-10-28. Land and water area: Census 2025 Gazetteer. Residents near a park: 2020 Census blocks. National Register: National Park Service. How TownRatings grades the outdoors →