A bird sitting on a nest of eggs.

Hiking Near Greenwood Lake, New York

Shorter Routes icon

Shorter Routes

These hikes keep it under 5 miles and climb less than 1,500 feet, making them ideal for quicker outings or lower-key days. Perfect for a morning stretch, a casual afternoon, or getting outside without committing to a big push. Don’t let the stats fool you — many still pack in great views and rewarding moments.

Sterling Fire Tower

Hike Route

Sterling Fire Tower

Dogs Allowed
easy
1.91 mi
+639 ft
Lakeville Ironworks Trail

Hike Route

Lakeville Ironworks Trail

Dogs Allowed
easy
1.05 mi
+134 ft
Dater Mountain Loop

Hike Route

Dater Mountain Loop

Less Crowded
moderate
4.77 mi
+1,039 ft
Tom Jones Loop

Hike Route

Tom Jones Loop

Views
moderate
4.68 mi
+1,488 ft
Mt Defiance

Hike Route

Mt Defiance

Birding
easy
2.08 mi
+429 ft
Diamond Mountain

Hike Route

Diamond Mountain

Birding
easy
0.06 mi
+0 ft
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Adventurous Routes

These routes go beyond 10 miles and are built for days when you want to cover more ground and push a little deeper. Expect longer distances, more effort, and bigger payoffs — whether that’s remote terrain, summit views, or a full-day challenge. Ideal for hikers looking to go farther and stay out longer.

The Highlands Trail - NJ Section

Hike Route

The Highlands Trail - NJ Section

Commonly Backpacked
extreme
123.36 mi
+17,324 ft
Terrace Pond North - South Loop

Hike Route

Terrace Pond North - South Loop

Lake
strenuous
10.65 mi
+1,784 ft
Tuxedo - Ramapo Torne - Dutch Dr loop

Hike Route

Tuxedo - Ramapo Torne - Dutch Dr loop

Fall Colors
extreme
14.52 mi
+3,690 ft
Pine Meadow Trail

Hike Route

Pine Meadow Trail

Lake
strenuous
13.21 mi
+1,881 ft
Stonetown Circular Trail

Hike Route

Stonetown Circular Trail

Lakefront
strenuous
11.16 mi
+3,093 ft
Bear Mountain-Harriman Loop

Hike Route

Bear Mountain-Harriman Loop

Fall Colors
extreme
20.23 mi
+4,502 ft

Other Nearby Routes

Not finding what you're looking for? These additional nearby hikes offer more ways to get outside and explore the area. With a mix of lengths, difficulty levels, and terrain, you're likely to find something that fits your plans for the day. And remember, you can always use the onX Route Builder to create your own adventure from scratch.

Sterling Forest Fire Tower Loop

Hike Route

Sterling Forest Fire Tower Loop

Lake
moderate
7.56 mi
+1,327 ft
West Ridge Loop

Hike Route

West Ridge Loop

Lake
moderate
6.27 mi
+1,330 ft
Bearfort Ridge and Surprise Lake

Hike Route

Bearfort Ridge and Surprise Lake

Birding
moderate
7.09 mi
+1,336 ft
Bearfort Ridge Loop

Hike Route

Bearfort Ridge Loop

Lake
moderate
5.58 mi
+1,023 ft
Appalachian Trail Boardwalk to Warwick Turnpike Shuttle

Hike Route

Appalachian Trail Boardwalk to Warwick Turnpike Shuttle

Fall Colors
moderate
8.27 mi
+1,859 ft
Tuxedo - Mt. Ivy Trail

Hike Route

Tuxedo - Mt. Ivy Trail

Lake
strenuous
8.63 mi
+1,697 ft