A bird sitting on a nest of eggs.

Hiking Near Woodbourne, 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.

Shawangunk Ridge Trail: Roosa Gap Section

Hike Route

Shawangunk Ridge Trail: Roosa Gap Section

easy
3.36 mi
+753 ft
Ice Caves

Hike Route

Ice Caves

Cave
easy
3.31 mi
+595 ft
Shawangunk Ridge Trail: Gobblers Knob Section

Hike Route

Shawangunk Ridge Trail: Gobblers Knob Section

Views
easy
2.26 mi
+697 ft
Minnewaska Lake Carriageway

Hike Route

Minnewaska Lake Carriageway

Birding
easy
1.74 mi
+202 ft
Labyrinth + Lemon Squeeze

Hike Route

Labyrinth + Lemon Squeeze

Lake
easy
0.87 mi
+471 ft
Ashokan Reservoir Promenade

Hike Route

Ashokan Reservoir Promenade

Views
easy
2.73 mi
+43 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.

Millbrook Mountain + Gertrude's Nose

Hike Route

Millbrook Mountain + Gertrude's Nose

Dogs Allowed
strenuous
12.26 mi
+2,315 ft
Romer - Pleasant - Cross Mountain Traverse

Hike Route

Romer - Pleasant - Cross Mountain Traverse

Views
strenuous
11.64 mi
+2,509 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.

Sam's Point and Verkeerderkill Falls Trail

Hike Route

Sam's Point and Verkeerderkill Falls Trail

Birding
moderate
8.43 mi
+943 ft
Fir and Big Indian Mountain

Hike Route

Fir and Big Indian Mountain

Fall Colors
strenuous
9.29 mi
+2,443 ft
Shawangunk Ridge Trail: Peterskill Section

Hike Route

Shawangunk Ridge Trail: Peterskill Section

Views
moderate
8.34 mi
+1,283 ft
Ashokan High Point

Hike Route

Ashokan High Point

Views
strenuous
8.6 mi
+2,244 ft
Gertrude's Nose Loop

Hike Route

Gertrude's Nose Loop

Birding
moderate
6.51 mi
+1,162 ft
West Approach of Slide Mountain

Hike Route

West Approach of Slide Mountain

Birding
moderate
5.31 mi
+1,776 ft