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.

Eshqua Bog Loop

Hike Route

Eshqua Bog Loop

easy
0.32 mi
+45 ft
Mount Peg

Hike Route

Mount Peg

easy
1.54 mi
+376 ft
Mt. Tom Loop

Hike Route

Mt. Tom Loop

Birding
strenuous
4.69 mi
+817 ft
Prosper Trail to The Pogue

Hike Route

Prosper Trail to The Pogue

easy
2.41 mi
+319 ft
Dana Hill

Hike Route

Dana Hill

easy
2.62 mi
+804 ft
Slack Hill Loop

Hike Route

Slack Hill Loop

easy
3.21 mi
+555 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.

Long Trail to Killington peak

Hike Route

Long Trail to Killington peak

extreme
12.07 mi
+3,204 ft
Baker Peak and Griffith Lake

Hike Route

Baker Peak and Griffith Lake

strenuous
10.1 mi
+2,455 ft
Monadnock - Sunapee Greenway

Hike Route

Monadnock - Sunapee Greenway

Birding
strenuous
48.01 mi
+10,460 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.

Pinnacle Overlook

Hike Route

Pinnacle Overlook

strenuous
8.23 mi
+2,516 ft
Windsor Trail to Mt Ascutney

Hike Route

Windsor Trail to Mt Ascutney

strenuous
5.08 mi
+2,558 ft
Futures Trail to Mount Ascutney

Hike Route

Futures Trail to Mount Ascutney

strenuous
8.02 mi
+2,997 ft
French's Ledges Outer Loop

Hike Route

French's Ledges Outer Loop

moderate
6.6 mi
+872 ft
Killington Loop

Hike Route

Killington Loop

moderate
5.02 mi
+1,785 ft
Ludlow Mountain

Hike Route

Ludlow Mountain

strenuous
5.84 mi
+1,938 ft