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Hiking Near Whitingham, 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 Olga Loop

Hike Route

Mt Olga Loop

easy
1.57 mi
+549 ft
Bishop Trail to Firetower

Hike Route

Bishop Trail to Firetower

easy
2.08 mi
+488 ft
Dutch Hill Ski Area Loop

Hike Route

Dutch Hill Ski Area Loop

easy
1.33 mi
+550 ft
Hogback Mountain

Hike Route

Hogback Mountain

easy
2.4 mi
+265 ft
Dunbar Brook Trail

Hike Route

Dunbar Brook Trail

River/Creek
easy
3.01 mi
+890 ft
Haystack Mountain (Wilmington)

Hike Route

Haystack Mountain (Wilmington)

moderate
4.1 mi
+1,042 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.

Haystack Mountain and Mount Snow

Hike Route

Haystack Mountain and Mount Snow

strenuous
11.64 mi
+2,406 ft
Long Trail to Lake Hancock

Hike Route

Long Trail to Lake Hancock

strenuous
12.3 mi
+2,292 ft
Long Trail to Glastenbury Lookout

Hike Route

Long Trail to Glastenbury Lookout

extreme
19.05 mi
+4,561 ft
West Ridge to Glastenbury Lookout

Hike Route

West Ridge to Glastenbury Lookout

extreme
18.39 mi
+4,349 ft
Greylock in the Round

Hike Route

Greylock in the Round

Historical
strenuous
11.51 mi
+3,016 ft
Stratton Mountain and Pond

Hike Route

Stratton Mountain and Pond

strenuous
11.07 mi
+2,184 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.

Corridor 9 to Dome Mountain

Hike Route

Corridor 9 to Dome Mountain

strenuous
8.35 mi
+1,984 ft
Spruce Mountain Trail

Hike Route

Spruce Mountain Trail

Scenic
moderate
6.17 mi
+1,251 ft
Little Pond

Hike Route

Little Pond

easy
5.12 mi
+480 ft
Broad Brook to Seth Warner Shelter

Hike Route

Broad Brook to Seth Warner Shelter

strenuous
8.22 mi
+1,436 ft
The Dome

Hike Route

The Dome

moderate
5 mi
+1,726 ft
Leyden Blueberry Fields

Hike Route

Leyden Blueberry Fields

Birding
moderate
5.5 mi
+995 ft