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Town Hall Chestertown NYPhoto: Novis-M · Public domain
A−Outdoors
Outdoors in Chester

Chester has 3,421 acres of parks, 1,113 for every 1,000 residents

67 miles of mapped trail cross Chester, 0.8 per square mile of land. The biggest trail networks: Lake George Wild Forest (8 mi), Vanderwhacker Mountain Wild Forest (4.6 mi). 7% of Chester’s land is conserved, about 4,000 acres.

Ahead of 79% of U.S. towns · #238 of 758 in New York. What drives it

Conserved land
7%
4,000 acres · of 84.2 sq mi of land
Trails
67 mi
0.8 per sq mi of land
Park land
3,421 ac
1,113 acres per 1,000 residents
Near a park
34%
of residents within ½ mile
Highest peak
2,093 ft
Green Hill
Lakes & rivers
15
7 beaches · 1 boat launch

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 79% of U.S. towns, #238 of 758 in New York. Park acres per resident hold the grade up; the share of residents near a park pulls it down.

A−
OutdoorsA character grade: shown, never part of Chester’s overall grade.
All U.S. towns we grade (21,298)Ahead of 79%
LessMore
New York towns of 2,500+ (758)Ahead of 69%
How sure. Graded on any three of the four inputs instead, the letter would range from B 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.

12
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 Lake George Wild Forest, with 8 miles. Directions go to the nearest trailhead or public parking.

Lake George Wild Forest

Managed by New York State Department of Environmental Conservation
1,571 acres8 mi of trail
Palmer Pond trailPalmer Pond paththree barrel trail (yellow/red)path (yellow)
Dog rules not recorded
Directionsto the parking lotWebsite ↗

Vanderwhacker Mountain Wild Forest

Managed by New York State Department of Environmental Conservation
1,474 acres4.6 mi of trail
snowmobile trailGreen Mountain Trail (Blue)Summer Trail (Orange)Bear Claw Pass Trail (Orange)
Dog rules not recorded
Directionsto the parking lotWebsite ↗
Who protects it

4,000 conserved acres

7% of Chester’s land. Who manages Chester’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.

State conservation4,991 ac
Land trusts & nonprofits450 ac
Town or city130 ac
Private owners18 ac
Other state land13 ac
Other or Unknown Local Government9 ac
Regional agency5 ac
State Conservation Area · 3,947 acPrivate Conservation · 450 acUnknown Easement · 439 acForest Stewardship Easement · 439 acState Recreation Area · 161 ac
Good to know

Conserved doesn’t always mean open to visitors. 446 acres are conservation easements, usually private land. Public access isn’t recorded for 9 of 32 parcels. The walks above are places people visit.

The biggest protected parcels
Parcel (PAD-US)Managed byAcresPublic access
Lake George Wild Forest
State Conservation Area
State conservation1,614Open
Vanderwhacker Mountain Wild Forest
State Conservation Area
State conservation1,492Open
State Conservation Area
State Conservation Area
State conservation771Restricted
Moxham Mountain
Private Conservation
Land trusts & nonprofits232Restricted
Scaroon Manor Campground
State Recreation Area
State conservation141Open
Town of Chester Land
Local Park
Town or city128Unknown
Hudson River Ice Meadows Preserve
Private Conservation
Land trusts & nonprofits85Open
Hudson River Ice Meadows
Private Conservation
Land trusts & nonprofits85Restricted
Finch Pruyn
State Conservation Area
State conservation67Restricted
Jenks Swamp Preserve
Private Conservation
Land trusts & nonprofits24Closed

5 smaller protected places aren’t shown.

Things to do

47 places to go in Chester

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

Peaks in Chester
Green Hill2,093 ft elevation
Directions
Henderson Mountain2,037 ft elevation
Directions
Bibby Mountain1,942 ft elevation
Directions
Ethan Mountain1,900 ft elevation
Directions
Round Top Mountain1,647 ft elevation
Directions
Kipp Mountain1,608 ft elevation
Directions
West Hill1,588 ft elevation
Directions
Catamount Hill1,581 ft elevation
Directions
9 more peaks
Beckman mountain1,572 ft elevation
Directions
Meade Mountain1,552 ft elevation
Directions
Panther Mountain1,503 ft elevation
Directions
McGann Mountain1,453 ft elevation
Directions
Sugarloaf Hill1,424 ft elevation · In Vanderwhacker Mountain Wild Forest
Directions
Huckleberry Mountain1,322 ft elevation
Directions
Campground Mountain1,299 ft elevation
Directions
Remington Mountain1,250 ft elevation
Directions
Signal Hill1,089 ft elevation
Directions
Trails & water

25 named trails and 15 lakes & rivers

Named trails
Unpaved · 45.8 mi
snowmobile trail2.5 mi
Perimeter Loop Trail1.6 mi
Summit Trail (Yellow)1.6 mi
Cunningham Ski Trail1.3 mi
Green Mountain Trail (Blue)1.3 mi
Panther mountain trail1.2 mi
Fish Loop Trail1.1 mi
Palmer Pond trail1.0 mi
Catamount Vista View Trail (Blue)1.0 mi
Meade mountain trail1.0 mi
15 more trails
Trout Brook Trail (Red)
1.0 mi
Ferriss Road Extension
0.9 mi
Cougar Hill Trail
0.9 mi
Kipp mountain trail
0.8 mi
Palmer Pond path
0.7 mi
Hidden Valley View Trail (Yellow)
0.7 mi
Side Hill Trail
0.7 mi
Chester Creek Trail
0.6 mi
Leanto Trail
0.6 mi
Dynamite Loop Trail
0.6 mi
three barrel trail (yellow/red)
0.6 mi
Only Way Trail (Blue)
0.5 mi
Beaver Stump Loop (Orange)
0.5 mi
East Ski Trail (Red)
0.4 mi
Ford Brook Trail (Yellow)
0.4 mi
Lakes & rivers tap for directions
Biking & sports

0.0 miles of bike routes

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

Courts & fields
4Soccer
4Baseball
2Tennis
1Basketball

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

History along the way

1 place on the National Register

The country’s official list of places worth saving (National Park Service).

History →
Chestertown Historic DistrictDistrict · listed 2025
About it
When to get out

The best walking months in Chester: 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.

JanFebMarAprMayJunJulAugSepOctNovDec
Daylight (h)9.310.411.813.414.715.415.114.012.410.99.68.9
High (°F)283240546775797870574534
Rain (in)3.12.63.43.83.64.24.14.13.54.13.53.7

February is the driest month (2.6 in) and July the warmest (highs of 79 °F). 4.2 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
Chester7%0.81,11334%A−
Horicon32%0.44,45444%A
Johnsburg61%0.715,01854%A
Pottersville— not graded: under 1,000 residents or part of its town
Thurman51%0.429,56024%A−
Warrensburg23%1.11,80383%A+
Minerva— not graded: under 1,000 residents or part of its town
North Creek— 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: Lake George Wild Forest, 8 miles; Vanderwhacker Mountain Wild Forest, 4.6 miles. Each one is on the map above, with directions to the nearest trailhead or parking.

How much of Chester is conserved land?

7% 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?

Lake George Wild Forest and Vanderwhacker Mountain Wild Forest don’t have dog rules recorded on the map; check the signs at the trailhead.

Is there public land near Chester?

249,004 acres of parks and open public land lie inside Chester or within 10 miles of it (PAD-US), 3,421 of them inside the town line.

How much outdoors does Chester have?

Ahead of 79% of U.S. towns on the Outdoors grade, #238 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 →