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Chester, NY, town hallPhoto: Daniel Case · CC BY-SA 3.0
AOutdoors
Outdoors in Chester

Chester has 2,480 acres of parks, 196 for every 1,000 residents

16% of Chester’s land is conserved, about 2,624 acres. The biggest trail networks: Goosepond Mountain State Park (7 mi), Chester Commons Park (0.6 mi). 19 miles of mapped trail cross Chester, 0.8 per square mile of land.

Ahead of 91% of U.S. towns · #115 of 758 in New York. What drives it

Conserved land
16%
2,624 acres · of 25.0 sq mi of land
Trails
19 mi
0.8 per sq mi of land
Park land
2,480 ac
196 acres per 1,000 residents
Near a park
76%
of residents within ½ mile
Bike routes
2.8 mi
2.8 mi paths
Highest peak
1,138 ft
Sugarloaf Mountain

What kind of outdoors town is Chester?

Read from the map. The page puts what stands out first.

Outdoors grade

How much outdoors does Chester have?

On conserved land, trails, park land and how close residents live to a park, Chester is ahead of 91% of U.S. towns, #115 of 758 in New York. 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 Chester’s overall grade.
All U.S. towns we grade (21,298)Ahead of 91%
LessMore
New York towns of 2,500+ (758)Ahead of 85%
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.

1234
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 Goosepond Mountain State Park, with 7 miles. Directions go to the nearest trailhead or public parking.

Goosepond Mountain State Park

Managed by New York State Office of Parks, Recreation and Historic Preservation
2,050 acres7 mi of trail
Goose Pond Mountain Trail
Dog rules not recorded
No trailhead mapped yetWebsite ↗

Chester Commons Park

Park
35 acres0.6 mi of trail
Chester Commons Hiking Trail
Dog rules not recorded
No trailhead mapped yet

Knapp's View

Park
91 acres
Dog rules not recorded
Directionsto the parking lot

Appalachian National Scenic Trail

Managed by National Park Service
22 acres0.2 mi of trail
Dogs usually limited
No trailhead mapped yetWebsite ↗
All 5 parks & preserves
Goosepond Mountain State Park2,050 acres · 7 mi of trail · New York State Office of Parks, Recreation and Historic Preservation
Chester Commons Park35 acres · 0.6 mi of trail
Appalachian National Scenic Trail22 acres · 0.2 mi of trail · National Park Service
Carpenter Park12 acres · 0.1 mi of trail
Knapp's View91 acres
Directions
Who protects it

2,624 conserved acres

16% of Chester’s land. Who manages Chester’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.

State parks2,053 ac
Land trusts & nonprofits435 ac
USDA easements (NRCS)161 ac
Other or Unknown Local Government148 ac
Town or city140 ac
County58 ac
National Park Service21 ac
State Park · 2,053 acAgricultural Easement · 326 acLocal Park · 173 acConservation Easement · 166 acLocal Resource Management Area · 126 ac
Good to know

Conserved doesn’t always mean open to visitors. 169 acres are conservation easements, usually private land. Public access isn’t recorded for 4 of 25 parcels. The walks above are places people visit.

The biggest protected parcels
Parcel (PAD-US)Managed byAcresPublic access
Goose Pond Mountain
State Park
State parks2,053Open
Orange County Land Trust Land
Private Conservation
Land trusts & nonprofits106Open
The School Of Practical Lands
Local Resource Management Area
Other or Unknown Local Government93Open
Town Of Chester Land
Local Park
Town or city83Unknown
Chester Town Lands
Local Resource Management Area
Other or Unknown Local Government30Open
Heritage Trail
Local Recreation Area
County29Open
County Of Orange Land
Local Park
County27Unknown
Chester Commons Park
Local Park
Other or Unknown Local Government22Open
Appalachian National Scenic Trail
National Scenic or Historic Trail
National Park Service20Open
Port Jervis City Lands
Local Park
Town or city19Open

5 smaller protected places aren’t shown.

Things to do

18 places to go in Chester

Beaches, playgrounds, peaks, falls and more. Pick a kind.

Peaks in Chester
Sugarloaf Mountain1,138 ft elevation
Directions
Goose Pond Mountain1,066 ft elevation · In Goosepond Mountain State Park
Directions
Snake Mountain965 ft elevation
Directions
Brimstone Mountain932 ft elevation
Directions
Bellvale Mountain846 ft elevation
Directions
Durland Hill840 ft elevation
Directions
Lazy Hill837 ft elevation
Directions
Pine Hill830 ft elevation
Directions

Plus 1 peak without a name on the map. Tap “Show all on map” to see it.

Trails & water

4 named trails

Named trails
Horses · 0.8 mi
Goose Pond Mountain Trail2.9 mi
Chester Commons Hiking Trail0.3 mi
Marsh Trail0.2 mi
Lutjens Alley0.1 mi
Biking & sports

2.8 miles of bike routes

Bike lanes are often missing from the map in smaller towns, so that number is likely low.

2.8 mi
off-road bike paths
Courts & fields
8Basketball
7Baseball
4Tennis
3Soccer
1Softball

Includes school and college facilities, which aren’t always open to the public.

History along the way

4 places on the National Register

The country’s official list of places worth saving (National Park Service). The map also marks 3 historic points from OpenStreetMap: plaques, memorials and old buildings.

History →
Yelverton Inn and StoreBuilding · listed 1980
About it
First Presbyterian Church of ChesterBuilding · listed 1998
About it
Fury Brook FarmBuilding · listed 2004
About it
Sugar Loaf Historic DistrictDistrict · listed 2024
About it
When to get out

The best walking months in Chester: April, 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.

JanFebMarAprMayJunJulAugSepOctNovDec
Daylight (h)9.510.611.813.314.515.114.913.812.411.09.89.2
High (°F)353847607078838174635140
Rain (in)3.32.63.73.73.64.74.34.44.44.43.43.9

February is the driest month (2.6 in) and July the warmest (highs of 83 °F). 4.7 inches fall in June, the wettest month. The climate in Chester →

Next door

Chester and its neighbors

Tap a town to see its outdoors.

TownConserved
of land
Trail mi
per sq mi
Park acres
per 1,000
Near a park
½ mile
Outdoors
Chester16%0.819676%A
Blooming Grove4%0.54975%B+
Goshen2%0.94071%B+
Warwick28%0.938369%A
Monroe22%0.810179%A
Walton Park— not graded: under 1,000 residents or part of its town

The four inputs of the Outdoors grade, from the engine; shares are of land, not water.

Questions about parks and trails in Chester

Where can I hike in Chester?

The longest trail networks: Goosepond Mountain State Park, 7 miles; Chester Commons Park, 0.6 miles; Appalachian National Scenic Trail, 0.2 miles. Each one is on the map above, with directions to the nearest trailhead or parking.

How much of Chester is conserved land?

16% of its land, against a typical 5% for a New York town and 4% nationally (PAD-US). Conserved doesn’t always mean open to visitors: easements are usually private land.

Are dogs allowed on Chester’s trails?

Goosepond Mountain State Park and Chester Commons Park don’t have dog rules recorded on the map; check the signs at the trailhead.

Where can I bike in Chester?

2.8 miles of bike routes are on the map: 2.8 of off-road paths.

Is there public land near Chester?

98,366 acres of parks and open public land lie inside Chester or within 10 miles of it (PAD-US), 2,500 of them inside the town line.

How much outdoors does Chester have?

Ahead of 91% of U.S. towns on the Outdoors grade, #115 of 758 in New York. 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 Chester neighbors.

Town Square →
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 →