Stewart State Forest
Nature preserve
1,131 acres11.6 mi of trail
Ant Hill TrailEscarpment TrailPower Line TrailDawn+1
Dog rules not recorded
Directionsto the parking lotWebsite ↗
Photo: Daniel Case · CC BY-SA 3.0AOutdoors
Outdoors in Montgomery
Montgomery has 2,363 acres of parks, 102 for every 1,000 residents
11% of Montgomery’s land is conserved, about 3,518 acres. The biggest trail networks: Stewart State Forest (11.6 mi), James W. Olley Park (1.3 mi). 38 miles of mapped trail cross Montgomery, 0.8 per square mile of land.
Ahead of 88% of U.S. towns · #142 of 758 in New York. What drives it
Conserved land
11%
3,518 acres · of 50.3 sq mi of land
Trails
38 mi
0.8 per sq mi of land
Park land
2,363 ac
102 acres per 1,000 residents
Near a park
78%
of residents within ½ mile
Bike routes
2.3 mi
2.3 mi paths
Lakes & rivers
7
1 boat launch
What kind of outdoors town is Montgomery?
Read from the map. The page puts what stands out first.
Outdoors grade
How much outdoors does Montgomery have?
On conserved land, trails, park land and how close residents live to a park, Montgomery is ahead of 88% of U.S. towns, #142 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 Montgomery’s overall grade.
Conserved land11% of the land · typical NY town 5% · U.S. 4%A−Trails0.8 miles of mapped trail per square mile of land (38 mi) · NY 0.4 · U.S. 0.4B+Park land102 acres of park per 1,000 residents (2,363 acres) · NY 31 · U.S. 13AParks close to home78% of residents within a half mile of a park · NY 70% · U.S. 72%B
All U.S. towns we grade (21,298)Ahead of 88%
LessMore
New York towns of 2,500+ (758)Ahead of 81%
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 Stewart State Forest, with 11.6 miles. Directions go to the nearest trailhead or public parking.
James W. Olley Park
Managed by Village of Walden
86 acres1.3 mi of trail
Long TrailShort TrailNature Trail
Dog rules not recorded
Directionsto the parking lot
All 14 parks & preserves
Stewart State Forest1,131 acres · 11.6 mi of trail
DirectionsJames W. Olley Park86 acres · 1.3 mi of trail · Village of Walden
DirectionsPleasure Ground Park36 acres · 0.4 mi of trail
DirectionsBrick House Museum County Park37 acres · 0.1 mi of trail
DirectionsVeterans Memorial Park14 acres · 0.1 mi of trail · Village of Montgomery
DirectionsMarcus "Mickey" Millspaugh Riverfront Park1 acres · 0.1 mi of trail
DirectionsMontgomery Town Park120 acres
DirectionsBenedict Farm Park38 acres
DirectionsBradley Park19 acres
DirectionsFrederick O Meyer Veterans Memorial Park12 acres
DirectionsWooster Memorial Grove Park7 acres
DirectionsRiver Front Park7 acres
Kimball Park1 acres
DirectionsMartin "Marty" Besdesky Playground1 acres · Village of Walden
Who protects it
3,518 conserved acres
11% of Montgomery’s land. Who manages Montgomery’s conserved land, from the USGS Protected Areas Database. Approximate, because parcels can overlap.
Land trusts & nonprofits3,248 ac
State conservation1,136 ac
Town or city677 ac
Other or Unknown Local Government387 ac
County370 ac
USDA easements (NRCS)333 ac
Private owners1 ac
Agricultural Easement · 1,529 acLocal Park · 1,322 acState Conservation Area · 1,136 acPrivate Conservation · 1,080 acConservation Easement · 924 ac
Good to know
Conserved doesn’t always mean open to visitors. 241 acres are conservation easements, usually private land. Public access isn’t recorded for 6 of 77 parcels. The walks above are places people visit.
The biggest protected parcels
| Parcel (PAD-US) | Managed by | Acres | Public access |
|---|---|---|---|
| Stewart State Forest State Conservation Area | State conservation | 1,136 | Open |
| Open Space Institute Land Private Conservation | Land trusts & nonprofits | 935 | Open |
| Winding Hills County Park Local Park | County | 299 | Open |
| Montgomery Town Of Land Local Park | Town or city | 274 | Unknown |
| Walden Village of Land Local Park | Town or city | 168 | Unknown |
| Orange County Land Trust Land Private Conservation | Land trusts & nonprofits | 145 | Open |
| Town Park Local Park | Other or Unknown Local Government | 114 | Open |
| Goshen Village Lands Local Resource Management Area | Other or Unknown Local Government | 113 | Open |
| Benedict Farm Park Local Park | Town or city | 102 | Open |
| James Olley Park Local Park | Other or Unknown Local Government | 99 | Open |
5 smaller protected places aren’t shown.
Things to do
27 places to go in Montgomery
Beaches, playgrounds, peaks, falls and more. Pick a kind.
Playgrounds in Montgomery
Danny Meyer Memorial PlaygroundIn Frederick O Meyer Veterans Memorial Park
DirectionsHopscotch Area
DirectionsKindergarten Playground
DirectionsMain Playground
DirectionsPlus 18 playgrounds without a name on the map. Tap “Show all on map” to see them.
Dog parks in Montgomery
1 dog park without a name on the map. Tap “Show all on map” to see it.
Boat launches in Montgomery
1 boat launch without a name on the map.
Scenic views in Montgomery
Peter's Point
DirectionsPicnic areas in Montgomery
1 picnic area without a name on the map.
Disc golf in Montgomery
James W. Olley Park Disc GolfIn James W. Olley Park · Village of Walden
DirectionsTrails & water
19 named trails and 7 lakes & rivers
Named trails
Open to bikes · 14.4 miHorses · 1.8 miUnpaved · 8.7 mi
Escarpment Trail1.4 mi
Power Line Trail1.4 mi
Ant Hill Trail1.3 mi
Dawn1.3 mi
Ant Ramble Trail1.1 mi
Pond Trail0.7 mi
Horse Trail0.6 mi
Long Trail0.5 mi
Big Trees Trail0.5 mi
Fiesta0.4 mi
9 more trails
Short Trail
0.3 miPond Extension
0.3 miKellys Pond Trail
0.3 miPine Root
0.2 miMeadow View Trail
0.1 miNature Trail
0.1 miColden Trail
0.1 miSnowmobile Trail
0.1 miCactus Trail
0.1 miLakes & rivers tap for directions
Biking & sports
2.3 miles of bike routes
Bike lanes are often missing from the map in smaller towns, so that number is likely low.
2.3 mi
off-road bike paths
Courts & fields
19Baseball
11Tennis
9Basketball
5Soccer
3Football
2Multi-sport
1Pickleball
1Skate park
Includes school and college facilities, which aren’t always open to the public.
History along the way
History →35 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.
Hill, Nathaniel, Brick HouseBuilding · listed 1978
About itBridge Street Historic DistrictDistrict · listed 1980
About itJohannes Miller HouseBuilding · listed 1980
About itMontgomery Worsted MillsBuilding · listed 1980
About itPatchett HouseBuilding · listed 1980
About itUnion Street-Academy Hill Historic DistrictDistrict · listed 1980
About itJohn Blake HouseBuilding · listed 1984
About itPeachcroftBuilding · listed 1995
About itDaniel Waring HouseBuilding · listed 1995
About itDickerson, Abraham, FarmhouseBuilding · listed 1995
About itGideon Pelton FarmBuilding · listed 1995
About itBenjamin Haines HouseBuilding · listed 1996
About it23 more on the History page.
When to get out
The best walking months in Montgomery: 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.
| Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Daylight (h) | 9.5 | 10.5 | 11.8 | 13.3 | 14.5 | 15.2 | 14.9 | 13.8 | 12.4 | 11.0 | 9.8 | 9.2 |
| High (°F) | 35 | 38 | 47 | 60 | 71 | 79 | 84 | 82 | 75 | 63 | 50 | 40 |
| Rain (in) | 3.0 | 2.5 | 3.4 | 3.6 | 3.5 | 4.5 | 4.1 | 4.2 | 4.3 | 4.3 | 3.2 | 3.6 |
February is the driest month (2.5 in) and July the warmest (highs of 84 °F). 4.5 inches fall in June, the wettest month. The climate in Montgomery →
Next door
Montgomery and its neighbors
Tap a town to see its outdoors.
Wallkill75 miNew Windsor41 miMontgomery38 miShawangunk15 miNewburgh12 miCrawford11 miHamptonburgh7.6 miMaybrook2.9 mi
| Town | Conserved of land | Trail mi per sq mi | Park acres per 1,000 | Near a park ½ mile | Outdoors |
|---|---|---|---|---|---|
| Montgomery | 11% | 0.8 | 102 | 78% | A |
| Crawford | 4% | 0.3 | 54 | 40% | B |
| Newburgh | — not graded: under 1,000 residents or part of its town | ||||
| Hamptonburgh | 8% | 0.3 | 198 | 40% | B+ |
| Shawangunk | 11% | 0.3 | 147 | 34% | B+ |
| New Windsor | 33% | 1.2 | 256 | 92% | A+ |
| Maybrook | 15% | 2.0 | 45 | 99%+ | A+ |
| Wallkill | 12% | 1.2 | 162 | 84% | A |
The four inputs of the Outdoors grade, from the engine; shares are of land, not water.
Questions about parks and trails in Montgomery
Where can I hike in Montgomery?
The longest trail networks: Stewart State Forest, 11.6 miles; James W. Olley Park, 1.3 miles; Pleasure Ground Park, 0.4 miles. Each one is on the map above, with directions to the nearest trailhead or parking.
How much of Montgomery is conserved land?
11% 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 Montgomery’s trails?
Stewart State Forest and James W. Olley Park don’t have dog rules recorded on the map; check the signs at the trailhead.
Where can I bike in Montgomery?
2.3 miles of bike routes are on the map: 2.3 of off-road paths.
Is there public land near Montgomery?
59,173 acres of parks and open public land lie inside Montgomery or within 10 miles of it (PAD-US), 2,363 of them inside the town line.
How much outdoors does Montgomery have?
Ahead of 88% of U.S. towns on the Outdoors grade, #142 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 Montgomery 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 →