A bird sitting on a nest of eggs.

Hiking Near Pittsfield, Vermont

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.

New Boston Trail

Hike Route

New Boston Trail

Birding
moderate
2.07 mi
+631 ft
Deer Leap Overlook

Hike Route

Deer Leap Overlook

Birding
moderate
1.9 mi
+583 ft
Mt. Tom Loop

Hike Route

Mt. Tom Loop

Birding
strenuous
4.69 mi
+861 ft
Sunset Ledge

Hike Route

Sunset Ledge

Commonly Backpacked
strenuous
0.75 mi
+59 ft
Gile Mountain

Hike Route

Gile Mountain

Dogs Allowed
easy
0.67 mi
+391 ft
Little Ascutney Mountain

Hike Route

Little Ascutney Mountain

Birding
moderate
3.06 mi
+1,050 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.

Pico Peak via Sherburne Pass Trail

Hike Route

Pico Peak via Sherburne Pass Trail

Birding
strenuous
5.41 mi
+1,798 ft
Mount Abraham and Lincoln Peak

Hike Route

Mount Abraham and Lincoln Peak

Birding
strenuous
6.13 mi
+2,197 ft