1
Stewart State Forest
Nature preserve
1,131 acres11.6 mi of trail
Ant Hill TrailEscarpment TrailPower Line TrailDawnPond Trail
Dog rules not recorded
Outdoors · Montgomery
Montgomery, NY parks, trails & bike paths
About 11% of Montgomery is conserved land, roughly 3,518 acres. There are about 38 miles of mapped trails, and the biggest networks are in Stewart State Forest (11.6 mi) and James W. Olley Park (1.3 mi).
Conserved land, trails, parks and bike routes in Montgomery, measured from OpenStreetMap and USGS data.
At a glance
Montgomery outdoors
Conserved land
11%
3,518 of 32,569 acres
Trails
38 mi
0.7 mi per sq mi · 17 on conserved land
Parks & preserves
14
151 conserved acres per 1,000 residents
Bike routes
2.3 mi
0.0 mi lanes · 2.3 mi off-road paths
Conserved land is a share of the whole town area. Bike lanes are often missing from the map in smaller towns, so that number is likely low.
Map
Conserved land, trails & bike routes
Tap a number or a place below to zoom in© OpenStreetMap contributors · USGS PAD-US
Places to walk
Parks & preserves with trails
Ranked by mapped trail miles. Directions go to the nearest marked trailhead or public parking.
2
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
3
Pleasure Ground Park
Park
36 acres0.4 mi of trail
Dog rules not recorded
DirectionsTo the parking lot
4
Montgomery Town Park
Park
120 acres
Dog rules not recorded
DirectionsTo the parking lot
All 14 parks & preserves
- Brick House Museum County Park37 ac · 0.1 mi trail · Directions
- Veterans Memorial Park14 ac · 0.1 mi trail · Directions
- Marcus "Mickey" Millspaugh Riverfront Park1 ac · 0.1 mi trail · Directions
- Benedict Farm Park38 ac · Directions
- Bradley Park19 ac · Directions
- Frederick O Meyer Veterans Memorial Park12 ac · Directions
- Wooster Memorial Grove Park7 ac · Directions
- River Front Park7 ac
- Kimball Park1 ac · Directions
- Martin "Marty" Besdesky Playground1 ac
Who protects the land
3,518 conserved acres
Who manages it, from PAD-US. Approximate, because parcels can overlap.
Conserved doesn't always mean open to visitors. 241 acres are conservation easements, which are usually private land. Public access isn't recorded for 6 of 77 parcels. The places listed above are parks and preserves people visit.
Biking & sports
Bike routes, courts & fields
- Painted or protected bike lanes0.0 mi
- Off-road bike paths2.3 mi
- Shoulders & shared lanes0.0 mi
Courts & fields
- Baseball19
- Tennis11
- Basketball9
- Soccer5
- Football3
- Multi-sport2
- Pickleball1
Counts include school and college facilities, which aren't always open to the public.
Next door
Montgomery and its neighbors
Towns whose outdoors data has been built so far.
| Town | Conserved | Trails | Parks & preserves |
|---|---|---|---|
| Montgomery | 10.8% | 37.8 mi | 14 |
| Crawford | 3.9% | 11.2 mi | 3 |
| Newburgh | 3.3% | 11.8 mi | 2 |
| Hamptonburgh | 7.7% | 7.6 mi | 4 |
| Shawangunk | 11% | 14.2 mi | 8 |
| New Windsor | 30.1% | 41.2 mi | 8 |
| Maybrook | 14.9% | 2.9 mi | 2 |
Trail talk
Conditions & tips from neighbors
No recent posts about Montgomery's trails yet. Muddy, icy, a bridge out, where to park: a quick post helps the next person.
Sources: trails, parks, preserves, courts and bike lanes © OpenStreetMap contributors (ODbL), map data as of 2026-09-28. Conserved land: USGS Gap Analysis Project, Protected Areas Database of the United States (PAD-US). Measured against the Census town boundary.
How we measure
"Trails" are OpenStreetMap paths, bridleways, public tracks and unpaved footways, plus footways inside a park or preserve or on a named trail route. Sidewalks are left out. Areas are counted on a 29.7-meter grid, so overlapping parcels count once. "Conserved" includes conservation easements, which protect land from development but are usually private property. Trailheads are the nearest marked trailhead, public parking lot or information board within about 150 meters of a preserve. Dog rules come from OpenStreetMap when someone has tagged them; otherwise we show what's typical for the land manager, or say the rules aren't recorded.