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Oblong Friends MeetinghouseOblong Friends Meetinghouse · Photo: Rolf Müller (User:Rolfmueller) · CC BY-SA 3.0
A−Outdoors
Outdoors in Pawling

Pawling has 915 acres of parks, 114 for every 1,000 residents

40 miles of mapped trail cross Pawling, 0.9 per square mile of land. The biggest trail networks: Pawling Nature Reserve (6.6 mi), Deer Pond Farm (6.1 mi). 9% of Pawling’s land is conserved, about 2,577 acres.

Ahead of 79% of U.S. towns · #229 of 758 in New York. What drives it

Conserved land
9%
2,577 acres · of 44.0 sq mi of land
Trails
40 mi
0.9 per sq mi of land
Park land
915 ac
114 acres per 1,000 residents
Near a park
41%
of residents within ½ mile
Bike routes
5.3 mi
5.3 mi paths
Highest peak
1,329 ft
Observatory Hill
Lakes & rivers
14

What kind of outdoors town is Pawling?

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

Outdoors grade

How much outdoors does Pawling have?

On conserved land, trails, park land and how close residents live to a park, Pawling is ahead of 79% of U.S. towns, #229 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 Pawling’s overall grade.
All U.S. towns we grade (21,298)Ahead of 79%
LessMore
New York towns of 2,500+ (758)Ahead of 70%
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.

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 Pawling Nature Reserve, with 6.6 miles. Directions go to the nearest trailhead or public parking.

Pawling Nature Reserve

Nature preserve
677 acres6.6 mi of trail
Blue LoopRidge TrailAppalachian TrailYellow Loop+1
Dog rules not recorded
Directionsto the parking lot

Deer Pond Farm

Managed by Connecticut Audubon Society
443 acres6.1 mi of trail
Big Bear TrailCarolyn's TrailGreenwoods TrailLedges Loop Trail+1
Dogs usually not allowed
Directionsto the trail sign

Friends of Great Swamp

Nature preserve
190 acres
Dog rules not recorded
No trailhead mapped yet

Depot Hill Multiple Use Area

Managed by New York State Department of Environmental Conservation
23 acres
Dog rules not recorded
No trailhead mapped yetWebsite ↗
All 6 parks & preserves
Pawling Nature Reserve677 acres · 6.6 mi of trail
Directions
Deer Pond Farm443 acres · 6.1 mi of trail · Connecticut Audubon Society
Directions
Friends of Great Swamp190 acres
Depot Hill Multiple Use Area23 acres · New York State Department of Environmental Conservation
Michael Ciaiola Conservation Area22 acres
Northwest Connecticut Land Conservancy5 acres
Directions
Who protects it

2,577 conserved acres

9% of Pawling’s land. Who manages Pawling’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.

Land trusts & nonprofits1,533 ac
National Park Service1,371 ac
Town or city777 ac
Private owners162 ac
State conservation23 ac
Regional Water Districts4 ac
Not recorded22 ac
Private Conservation · 1,657 acNational Scenic or Historic Trail · 1,037 acLocal Park · 777 acConservation Easement · 349 acPrivate Other or Unknown · 34 ac
Good to know

Conserved doesn’t always mean open to visitors. 139 acres are conservation easements, usually private land. Public access isn’t recorded for 6 of 21 parcels. The walks above are places people visit.

The biggest protected parcels
Parcel (PAD-US)Managed byAcresPublic access
Pawling Nature Reserve
Private Conservation
Land trusts & nonprofits1,352Open
Appalachian National Scenic Trail
National Scenic or Historic Trail
National Park Service1,037Open
Town of Pawling Land
Local Park
Town or city370Unknown
Lakeside Park
Local Park
Town or city291Open
Private Lands
Private Conservation
Private owners162Closed
Great Swamp Preserve
Private Conservation
Land trusts & nonprofits138Closed
Edward R Murrow Park
Local Park
Town or city71Open
Village Of Pawling Land
Local Park
Town or city46Unknown
Oblong Land Conservancy Lands
Private Other or Unknown
Land trusts & nonprofits28Closed
Depot Hill Multiple Use Area
State Resource Management Area
State conservation23Open

2 smaller protected places aren’t shown.

Things to do

21 places to go in Pawling

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

Peaks in Pawling
Observatory Hill1,329 ft elevation
Directions
Branch Hill1,214 ft elevation
Directions
Seeley Hill1,207 ft elevation
Directions
West Mountain1,181 ft elevation
Directions
Pawling Mountain1,132 ft elevation
Directions
Purgatory Hill1,014 ft elevation
Directions
Mizzen Top971 ft elevation
Directions
Mount Tom965 ft elevation
Directions
1 more peak
Corbin Hill840 ft elevation
Directions

Plus 8 peaks without a name on the map.

Trails & water

21 named trails and 14 lakes & rivers

Named trails
Unpaved · 1.4 mi
Blue Loop1.9 mi
Big Bear Trail1.7 mi
Ridge Trail1.5 mi
Appalachian Trail1.4 mi
Yellow Loop1.1 mi
Carolyn's Trail0.9 mi
Nuclear Lake Trail0.7 mi
Greenwoods Trail0.6 mi
Ledges Loop Trail0.6 mi
Kirkby View Trail0.4 mi
11 more trails
Bruce's Trail
0.3 mi
Appalachian Trail / Yellow Loop
0.3 mi
David Beers Trail
0.3 mi
Hurd's Corner Entrance Trail
0.3 mi
Meadow Trail
0.3 mi
Coyote Trail
0.2 mi
Bobby's Field
0.2 mi
Chris' Trail
0.2 mi
Wolf Oaks Trail
0.2 mi
Ridge Trail / Blue Loop
0.2 mi
Agneil Trail
0.1 mi
Lakes & rivers tap for directions
Biking & sports

5.3 miles of bike routes

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

5.3 mi
off-road bike paths
Courts & fields
17Tennis
9Soccer
8Baseball
6Basketball
3Football

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

History along the way

3 places on the National Register

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

History →
Oblong Friends MeetinghouseBuilding · listed 1973
About it
John Kane HouseBuilding · listed 1980
About it
Akin Free LibraryBuilding · listed 1991
About it
When to get out

The best walking months in Pawling: April to June, August and 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)9.510.511.813.314.515.214.913.812.411.09.89.2
High (°F)353847607079838174635040
Rain (in)3.32.83.83.83.84.44.54.34.44.73.74.0

February is the driest month (2.8 in) and July the warmest (highs of 83 °F). 4.7 inches fall in October, the wettest month. The climate in Pawling →

Next door

Pawling and its neighbors

Pawling has the second most mapped trails of the 7 towns around it. 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
Pawling9%0.911441%A−
Beekman19%0.46744%A−
Patterson21%1.015473%A
Dover6%0.312256%B+
East Fishkill10%0.52669%B+
Kent39%1.740983%A+

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

Questions about parks and trails in Pawling

Where can I hike in Pawling?

The longest trail networks: Pawling Nature Reserve, 6.6 miles; Deer Pond Farm, 6.1 miles. Each one is on the map above, with directions to the nearest trailhead or parking.

How much of Pawling is conserved land?

9% 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 Pawling’s trails?

Pawling Nature Reserve and Deer Pond Farm don’t have dog rules recorded on the map; check the signs at the trailhead.

Where can I bike in Pawling?

5.3 miles of bike routes are on the map: 5.3 of off-road paths.

Is there public land near Pawling?

31,019 acres of parks and open public land lie inside Pawling or within 10 miles of it (PAD-US), 1,958 of them inside the town line.

How much outdoors does Pawling have?

Ahead of 79% of U.S. towns on the Outdoors grade, #229 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 Pawling 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 →