A bird sitting on a nest of eggs.

Hiking Near South Woodstock, 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.

Mt. Tom Loop

Hike Route

Mt. Tom Loop

Birding
strenuous
4.69 mi
+861 ft
Little Ascutney Mountain

Hike Route

Little Ascutney Mountain

Birding
moderate
3.06 mi
+1,050 ft
Deer Leap Overlook

Hike Route

Deer Leap Overlook

Birding
moderate
1.9 mi
+583 ft
Gile Mountain

Hike Route

Gile Mountain

Dogs Allowed
easy
0.67 mi
+391 ft
Moose Mountain Trail

Hike Route

Moose Mountain Trail

Birding
moderate
4.04 mi
+1,090 ft
New Boston Trail

Hike Route

New Boston Trail

Birding
moderate
2.07 mi
+631 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.

Monadnock - Sunapee Greenway

Hike Route

Monadnock - Sunapee Greenway

Birding
strenuous
47.98 mi
+10,455 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
Smarts Mountain

Hike Route

Smarts Mountain

Views
strenuous
7.54 mi
+2,468 ft
Mount Sunapee via Newbury Trail

Hike Route

Mount Sunapee via Newbury Trail

Lake
moderate
6.59 mi
+2,114 ft
Mt. Cardigan Super Loop

Hike Route

Mt. Cardigan Super Loop

Birding
strenuous
9.03 mi
+3,243 ft