Mount Greylock State Reservation
Managed by Division of State Parks and Recreation
1,542 acres9.9 mi of trail
Woodason Spring TrailAppalachian TrailNorthrup TrailRed Gate Trail+1
Dog rules not recorded
Directionsto the parking lot
Photo: John Phelan · CC BY 3.0A+Outdoors
Outdoors in Cheshire
Cheshire has 5,697 acres of parks, 1,771 for every 1,000 residents
40% of Cheshire’s land is conserved, about 6,779 acres. 23 miles of mapped trail cross Cheshire, 0.9 per square mile of land. The biggest trail networks: Mount Greylock State Reservation (9.9 mi), Appalachian Trail Corridor (3.4 mi), Cheshire Water Company Land (3.2 mi).
Ahead of 96% of U.S. towns · #150 of 283 in Massachusetts. What drives it
Conserved land
40%
6,779 acres · of 26.8 sq mi of land
Trails
23 mi
0.9 per sq mi of land
Park land
5,697 ac
1,771 acres per 1,000 residents
Near a park
79%
of residents within ½ mile
Bike routes
6.4 mi
6.4 mi paths
Highest peak
2,566 ft
Rounds Rock
Lakes & rivers
3
2 boat launches
What kind of outdoors town is Cheshire?
Read from the map. The page puts what stands out first.
Room to roam1,771 acres of park per 1,000 residents; the typical U.S. town has 13.Land that stays wild40% of the land is conserved; a typical Massachusetts town, 21%.A trail town0.9 miles of mapped trail per square mile of land, more than 77% of U.S. towns.History along the way5 places on the National Register.
Outdoors grade
How much outdoors does Cheshire have?
On conserved land, trails, park land and how close residents live to a park, Cheshire is ahead of 96% of U.S. towns, #150 of 283 in Massachusetts. All four inputs are above most U.S. towns; park acres per resident rank highest, the share of residents near a park lowest.
A+
OutdoorsA character grade: shown, never part of Cheshire’s overall grade.
Conserved land40% of the land · typical MA town 21% · U.S. 4%A+Trails0.9 miles of mapped trail per square mile of land (23 mi) · MA 1.9 · U.S. 0.4A−Park land1,771 acres of park per 1,000 residents (5,697 acres) · MA 91 · U.S. 13A+Parks close to home79% of residents within a half mile of a park · MA 93% · U.S. 72%B
All U.S. towns we grade (21,298)Ahead of 96%
LessMore
Massachusetts towns of 2,500+ (283)Ahead of 47%
Massachusetts towns conserve more land than most (a typical one, 21%; the U.S., 4%), so Cheshire’s 40% is ahead of 90% of Massachusetts towns, while its trails per square mile lead 16% 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 Mount Greylock State Reservation, with 9.9 miles. Directions go to the nearest trailhead or public parking.
Appalachian Trail Corridor
Managed by National Park Service
327 acres3.4 mi of trail
Appalachian TrailNothch Road access trail
Dogs usually limited
Directionsto the parking lot
Cheshire Water Company Land
Managed by Town of Cheshire Water Commission
641 acres3.2 mi of trail
Woodason Spring Trail
Dog rules not recorded
Directionsto the parking lot
Chalet Wildlife Management Area
Managed by Department of Fish And Game
2,423 acres1.7 mi of trail
Nothch Road access trail
Dog rules not recorded
Directionsto Parking for Cheshire Cobbles hike
All 8 parks & preserves
Mount Greylock State Reservation1,542 acres · 9.9 mi of trail · Division of State Parks and Recreation
DirectionsAppalachian Trail Corridor327 acres · 3.4 mi of trail · National Park Service
DirectionsCheshire Water Company Land641 acres · 3.2 mi of trail · Town of Cheshire Water Commission
DirectionsChalet Wildlife Management Area2,423 acres · 1.7 mi of trail · Department of Fish And Game
DirectionsAdams Fire District Watershed Land20 acres · 0.1 mi of trail
Stafford Hill Wildlife Management Area891 acres · Department of Fish and Game
Savoy Wildlife Management Area19 acres
Stafford Hill Memorial2 acres
Who protects it
6,779 conserved acres
40% of Cheshire’s land. Who manages Cheshire’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.
Other state land1,456 ac
National Park Service344 ac
USDA easements (NRCS)114 ac
State fish & wildlife104 ac
Town or city1 ac
Not recorded5,709 ac
State Conservation Area · 3,435 acAgricultural Easement · 1,570 acState Park · 1,529 acWatershed Protection Area · 692 acNational Scenic or Historic Trail · 329 ac
Good to know
Conserved doesn’t always mean open to visitors. 745 acres are conservation easements, usually private land. Public access isn’t recorded for 1 of 80 parcels. The walks above are places people visit.
The biggest protected parcels
| Parcel (PAD-US) | Managed by | Acres | Public access |
|---|---|---|---|
| Chalet Wildlife Management Area State Conservation Area | Not recorded | 2,563 | Open |
| Mount Greylock State Reservation State Park | Not recorded | 1,529 | Open |
| Stafford Hill Wildlife Management Area State Conservation Area | Not recorded | 854 | Open |
| Cheshire Water Company Land Watershed Protection Area | Not recorded | 638 | Open |
| Appalachian National Scenic Trail National Scenic or Historic Trail | National Park Service | 329 | Open |
| Cheshire Rod And Gun Club Private Other or Unknown | Not recorded | 86 | Restricted |
| Adams Fire District Land Watershed Protection Area | Not recorded | 53 | Unknown |
| Hoosac Valley Regional High School Athletic Fields Research or Educational Area | Not recorded | 36 | Open |
| Savoy Wildlife Management Area State Conservation Area | Not recorded | 18 | Open |
| Cheshire Cemetery Local Historic or Cultural Area | Not recorded | 18 | Open |
5 smaller protected places aren’t shown.
Things to do
19 places to go in Cheshire
Beaches, playgrounds, peaks, falls and more. Pick a kind.
Playgrounds in Cheshire
Cheshire Elementary Playground
DirectionsPlus 2 playgrounds without a name on the map. Tap “Show all on map” to see them.
Boat launches in Cheshire
Cheshire Boat Launch
DirectionsPlus 1 boat launch without a name on the map. Tap “Show all on map” to see it.
Fishing spots in Cheshire
4 fishing spots without a name on the map.
Waterfalls in Cheshire
Cascade on South BrookIn Chalet Wildlife Management Area
DirectionsScenic views in Cheshire
1 scenic view without a name on the map.
Peaks in Cheshire
Rounds Rock2,566 ft elevation · In Mount Greylock State Reservation
DirectionsNorth Mountain2,182 ft elevation · In Appalachian Trail Corridor
DirectionsCole Mountain2,110 ft elevation
DirectionsThe Cobbles1,841 ft elevation · In Appalachian Trail Corridor
DirectionsStafford Hill1,627 ft elevation · In Stafford Hill Wildlife Management Area
DirectionsMount Amos1,506 ft elevation · In Stafford Hill Wildlife Management Area
DirectionsCheshire Harbor Hill1,280 ft elevation
DirectionsCampgrounds in Cheshire
Father Tom CampsiteHours: May 1-Oct 30
DirectionsTrails & water
8 named trails and 3 lakes & rivers
Named trails
Unpaved · 12.6 mi
Appalachian Trail5.7 mi
Woodason Spring Trail3.3 mi
Red Gate Trail1.1 mi
Northrup Trail0.7 mi
Nothch Road access trail0.4 mi
Rounds Rock Trail0.4 mi
Stage Trail0.3 mi
Jones Nose Trail0.2 mi
Lakes & rivers tap for directions
Biking & sports
6.4 miles of bike routes
Bike lanes are often missing from the map in smaller towns, so that number is likely low.
6.4 mi
off-road bike paths
Courts & fields
5Baseball
2Basketball
2Soccer
1Football
Includes school and college facilities, which aren’t always open to the public.
History along the way
History →5 places on the National Register
The country’s official list of places worth saving (National Park Service). The map also marks 2 historic points from OpenStreetMap: plaques, memorials and old buildings.
When to get out
The best walking months in Cheshire: May and July
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) | 31 | 34 | 43 | 56 | 68 | 76 | 81 | 79 | 72 | 59 | 47 | 36 |
| Rain (in) | 3.1 | 2.6 | 3.3 | 3.5 | 3.8 | 4.6 | 4.3 | 4.4 | 4.6 | 4.4 | 3.4 | 3.7 |
February is the driest month (2.6 in) and July the warmest (highs of 81 °F). 4.6 inches fall in June, the wettest month. The climate in Cheshire →
Next door
Cheshire and its neighbors
Tap a town to see its outdoors.
| Town | Conserved of land | Trail mi per sq mi | Park acres per 1,000 | Near a park ½ mile | Outdoors |
|---|---|---|---|---|---|
| Cheshire | 40% | 0.9 | 1,771 | 79% | A+ |
| Lanesborough | 34% | 1.9 | 620 | 67% | A+ |
| New Ashford | — not graded: under 1,000 residents or part of its town | ||||
| Windsor | — not graded: under 1,000 residents or part of its town | ||||
| Savoy | — not graded: under 1,000 residents or part of its town | ||||
| Dalton | 52% | 1.3 | 608 | 92% | A+ |
The four inputs of the Outdoors grade, from the engine; shares are of land, not water.
Questions about parks and trails in Cheshire
Where can I hike in Cheshire?
The longest trail networks: Mount Greylock State Reservation, 9.9 miles; Appalachian Trail Corridor, 3.4 miles; Cheshire Water Company Land, 3.2 miles; Chalet Wildlife Management Area, 1.7 miles. Each one is on the map above, with directions to the nearest trailhead or parking.
How much of Cheshire is conserved land?
40% 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 Cheshire’s trails?
Mount Greylock State Reservation and Appalachian Trail Corridor don’t have dog rules recorded on the map; check the signs at the trailhead.
Where can I bike in Cheshire?
6.4 miles of bike routes are on the map: 6.4 of off-road paths.
Is there public land near Cheshire?
115,369 acres of parks and open public land lie inside Cheshire or within 10 miles of it (PAD-US), 5,945 of them inside the town line.
How much outdoors does Cheshire have?
Ahead of 96% of U.S. towns on the Outdoors grade, #150 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 Cheshire 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 →