Hiking TrailsUnited States of AmericaNorth Bennington, Vermont

Hiking Trails
Near North Bennington, Vermont

Regional Classics Icon

Regional Classics

Discover the must-do hikes in the area, handpicked and curated by local experts who know the trails best. These routes are beloved for good reason, offering standout scenery, rewarding terrain, and detailed descriptions with tips that tell you exactly what to expect. Whether you are visiting for the first time or are a local doing them on repeat, they offer a reliable and memorable hiking experience.

The Long Trail (Division 2)

Classic Hike Route

The Long Trail (Division 2)

Birding
strenuous
21.04 mi
+4,994 ft
The Long Trail (Division 1)

Classic Hike Route

The Long Trail (Division 1)

Birding
moderate
13.34 mi
+2,498 ft
The Long Trail (Division 3)

Classic Hike Route

The Long Trail (Division 3)

Birding
strenuous
21.5 mi
+4,411 ft
The Long Trail (Division 4)

Classic Hike Route

The Long Trail (Division 4)

Birding
strenuous
19.67 mi
+3,325 ft
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.

Mile Around Woods

Hike Route

Mile Around Woods

easy
2.8 mi
+195 ft
Frost Trail to Lake Paran

Hike Route

Frost Trail to Lake Paran

easy
4 mi
+384 ft
Mt Anthony from Everett Mansion

Hike Route

Mt Anthony from Everett Mansion

moderate
2.47 mi
+1,263 ft
Waters Hill Cemetery

Hike Route

Waters Hill Cemetery

easy
1.82 mi
+402 ft
Harmon Hill Vista

Hike Route

Harmon Hill Vista

moderate
3.23 mi
+1,085 ft
Long Trail to Maple Hill

Hike Route

Long Trail to Maple Hill

moderate
4.15 mi
+1,355 ft
Logo

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.

West Ridge to Glastenbury Lookout

Hike Route

West Ridge to Glastenbury Lookout

extreme
18.39 mi
+4,362 ft
Long Trail to Glastenbury Lookout

Hike Route

Long Trail to Glastenbury Lookout

extreme
19.05 mi
+4,563 ft
The Long Trail (Division 2)

Classic Hike Route

The Long Trail (Division 2)

Birding
strenuous
21.04 mi
+4,994 ft
The Long Trail (Division 1)

Classic Hike Route

The Long Trail (Division 1)

Birding
moderate
13.34 mi
+2,498 ft
Stratton Mountain and Pond

Hike Route

Stratton Mountain and Pond

strenuous
11.07 mi
+2,184 ft
The Long Trail (Division 3)

Classic Hike Route

The Long Trail (Division 3)

Birding
strenuous
21.5 mi
+4,411 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.

Bald Mountain (Bennington)

Hike Route

Bald Mountain (Bennington)

moderate
5.87 mi
+1,719 ft
Little Pond

Hike Route

Little Pond

easy
5.12 mi
+469 ft
The Dome

Hike Route

The Dome

moderate
5 mi
+1,726 ft
Broad Brook to Seth Warner Shelter

Hike Route

Broad Brook to Seth Warner Shelter

strenuous
8.22 mi
+1,421 ft
Corridor 9 to Dome Mountain

Hike Route

Corridor 9 to Dome Mountain

strenuous
8.35 mi
+1,985 ft
Branch Pond to Bourn Pond

Hike Route

Branch Pond to Bourn Pond

moderate
9.03 mi
+931 ft