A bird sitting on a nest of eggs.

Hiking Near Westport, 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.

Coon Mountain and Hidden Valley

Hike Route

Coon Mountain and Hidden Valley

easy
1.98 mi
+603 ft
Twin Valleys to Hornbeam Hill

Hike Route

Twin Valleys to Hornbeam Hill

easy
2.2 mi
+550 ft
North and South Boquet

Hike Route

North and South Boquet

moderate
4.97 mi
+936 ft
McDonough Point

Hike Route

McDonough Point

easy
0.84 mi
+88 ft
East Trail to Snake Mountain

Hike Route

East Trail to Snake Mountain

moderate
4.51 mi
+1,103 ft
Snake Mountain

Hike Route

Snake Mountain

Fall Colors
moderate
3.91 mi
+1,001 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.

Trail Around Middlebury

Hike Route

Trail Around Middlebury

strenuous
16.24 mi
+1,238 ft
Nippletop and Dial via Elk Pass

Hike Route

Nippletop and Dial via Elk Pass

Commonly Backpacked
strenuous
12.73 mi
+4,265 ft
Gothics + Armstrong

Hike Route

Gothics + Armstrong

Views
extreme
12.23 mi
+3,820 ft
The Wolfjaws

Hike Route

The Wolfjaws

Less Crowded
extreme
11.9 mi
+4,521 ft
Colvin and Blake

Hike Route

Colvin and Blake

Views
extreme
13.89 mi
+4,247 ft
Gill Brook Trail

Hike Route

Gill Brook Trail

Waterfall
extreme
12.65 mi
+3,579 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.

Rocky Peak Ridge and Giant Mountain Out and Back

Hike Route

Rocky Peak Ridge and Giant Mountain Out and Back

Views
strenuous
7.51 mi
+4,666 ft
Shelburne Farms Loop

Hike Route

Shelburne Farms Loop

Fall Colors
moderate
6.04 mi
+496 ft
Indian Head + Fishhawk Cliffs

Hike Route

Indian Head + Fishhawk Cliffs

Views
strenuous
9.09 mi
+1,522 ft
Lower Wolfjaw Mountain

Hike Route

Lower Wolfjaw Mountain

Dogs Allowed
strenuous
9.44 mi
+3,224 ft
Rainbow Falls on the Adirondack Mountain Reserve

Hike Route

Rainbow Falls on the Adirondack Mountain Reserve

Dogs Allowed
moderate
8.73 mi
+1,230 ft
Big Slide Via The Brothers

Hike Route

Big Slide Via The Brothers

Views
strenuous
6.83 mi
+3,198 ft