A bird sitting on a nest of eggs.

Hiking Near Montgomery, 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.

Crystal Lake to Snake Hill

Hike Route

Crystal Lake to Snake Hill

easy
2.59 mi
+543 ft
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
strenuous
3.31 mi
+595 ft
Sackett Ridge - Golden Ridge Loop

Hike Route

Sackett Ridge - Golden Ridge Loop

Views
moderate
4.34 mi
+887 ft
Black Rock

Hike Route

Black Rock

Views
moderate
3.57 mi
+1,014 ft
Stillman-Bluebird Loop

Hike Route

Stillman-Bluebird Loop

Spring
strenuous
4.55 mi
+1,077 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
Bear Mountain-Harriman Loop

Hike Route

Bear Mountain-Harriman Loop

Fall Colors
strenuous
20.23 mi
+4,502 ft
1777 Trail

Hike Route

1777 Trail

Lake
strenuous
13.97 mi
+2,590 ft
Manny's Swiss Army Knife Route

Hike Route

Manny's Swiss Army Knife Route

Birding
strenuous
14.4 mi
+3,518 ft
Illinois Mountain

Hike Route

Illinois Mountain

Birding
moderate
11.34 mi
+1,490 ft
Bear Mountain Loop

Hike Route

Bear Mountain Loop

Lake
strenuous
10.99 mi
+2,857 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.

Stewart State Forest South Loop

Hike Route

Stewart State Forest South Loop

easy
5.77 mi
+461 ft
Highland Lakes Loop

Hike Route

Highland Lakes Loop

easy
5.06 mi
+489 ft
Schunnemunk Highlight - Otterkill to Megalith Loop

Hike Route

Schunnemunk Highlight - Otterkill to Megalith Loop

Birding
strenuous
7.44 mi
+1,830 ft
Trestle Trail and Megaliths

Hike Route

Trestle Trail and Megaliths

Views
strenuous
8.39 mi
+1,972 ft
Jessup/Highlands/Long Path Trail

Hike Route

Jessup/Highlands/Long Path Trail

Less Crowded
moderate
9.79 mi
+1,624 ft
The Long Path: Gonzaga Park to Schunemunk State Park

Hike Route

The Long Path: Gonzaga Park to Schunemunk State Park

Views
strenuous
8.44 mi
+1,362 ft