A bird sitting on a nest of eggs.

Hiking Near Pleasant Valley, 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.

Roosevelt Farm Loop

Hike Route

Roosevelt Farm Loop

easy
2.77 mi
+108 ft
Red Wing Lakes Loop

Hike Route

Red Wing Lakes Loop

moderate
4.65 mi
+777 ft
Walkway Over The Hudson

Hike Route

Walkway Over The Hudson

Dogs Allowed
easy
1.46 mi
+308 ft
FDR Cove and Forest

Hike Route

FDR Cove and Forest

easy
2.7 mi
+234 ft
Franny Reese Loop

Hike Route

Franny Reese Loop

easy
3.21 mi
+417 ft
Slabsides

Hike Route

Slabsides

easy
3.68 mi
+322 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.

Illinois Mountain

Hike Route

Illinois Mountain

Birding
moderate
11.34 mi
+1,490 ft
Millbrook Mountain + Gertrude's Nose

Hike Route

Millbrook Mountain + Gertrude's Nose

Dogs Allowed
strenuous
12.26 mi
+2,315 ft
The Devil's Path

Hike Route

The Devil's Path

Birding
strenuous
21.83 mi
+8,327 ft
1777 Trail

Hike Route

1777 Trail

Lake
strenuous
13.97 mi
+2,590 ft
Kaaterskill High Peak

Hike Route

Kaaterskill High Peak

Birding
strenuous
12.86 mi
+3,690 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.

Norrie Point Loop

Hike Route

Norrie Point Loop

easy
5.08 mi
+337 ft
Louisa Pond Loop via White-Red-Blue Trails

Hike Route

Louisa Pond Loop via White-Red-Blue Trails

Views
moderate
5.41 mi
+1,086 ft
West Mountain State Forest Loop

Hike Route

West Mountain State Forest Loop

moderate
5.26 mi
+897 ft
Sierra and Freedom Loop

Hike Route

Sierra and Freedom Loop

easy
5.76 mi
+114 ft
Bonticou Crag and Table Rocks

Hike Route

Bonticou Crag and Table Rocks

Views
moderate
5.35 mi
+1,160 ft
Shawangunk Ridge Trail: Mohonk Preserve Section

Hike Route

Shawangunk Ridge Trail: Mohonk Preserve Section

Views
moderate
7.59 mi
+1,564 ft