A bird sitting on a nest of eggs.

Hiking Near Upper Red Hook, 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.

Trivoli Bays Loop

Hike Route

Trivoli Bays Loop

easy
3.03 mi
+444 ft
Esopus Bend Loop

Hike Route

Esopus Bend Loop

easy
4.43 mi
+402 ft
Keep Loop

Hike Route

Keep Loop

easy
2.21 mi
+71 ft
Thompson Pond and Stissing Fire Tower Loop

Hike Route

Thompson Pond and Stissing Fire Tower Loop

easy
2.53 mi
+913 ft
Buttercup Farm Loop

Hike Route

Buttercup Farm Loop

easy
4.61 mi
+340 ft
Esopus Meadows Preserve Loop

Hike Route

Esopus Meadows Preserve Loop

easy
1.38 mi
+215 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.

Kaaterskill High Peak

Hike Route

Kaaterskill High Peak

Birding
strenuous
12.86 mi
+3,690 ft
The Devil's Path

Hike Route

The Devil's Path

Birding
strenuous
21.83 mi
+8,327 ft
Devil's Path East

Hike Route

Devil's Path East

Views
extreme
10.66 mi
+3,862 ft
Illinois Mountain

Hike Route

Illinois Mountain

Birding
moderate
11.34 mi
+1,490 ft
Romer - Pleasant - Cross Mountain Traverse

Hike Route

Romer - Pleasant - Cross Mountain Traverse

Views
strenuous
11.64 mi
+2,509 ft
Millbrook Mountain + Gertrude's Nose

Hike Route

Millbrook Mountain + Gertrude's Nose

Dogs Allowed
strenuous
12.26 mi
+2,315 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.

All Trails Loop

Hike Route

All Trails Loop

Fall Colors
moderate
8.2 mi
+787 ft
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
Kite Hill-Fox HIll and Charcoal Loop

Hike Route

Kite Hill-Fox HIll and Charcoal Loop

moderate
5.24 mi
+584 ft
Rip's Rock Loop

Hike Route

Rip's Rock Loop

moderate
5.06 mi
+1,011 ft
Bear Mountain

Hike Route

Bear Mountain

Birding
moderate
5.23 mi
+1,555 ft