A bird sitting on a nest of eggs.

Hiking Near Chittenden, 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.

Leffert Pond Loop

Hike Route

Leffert Pond Loop

easy
2.82 mi
+120 ft
New Boston Trail

Hike Route

New Boston Trail

Birding
moderate
2.07 mi
+638 ft
Deer Leap Loop

Hike Route

Deer Leap Loop

moderate
3.1 mi
+1,052 ft
Deer Leap Overlook

Hike Route

Deer Leap Overlook

Birding
moderate
1.9 mi
+588 ft
Pesky Cairn

Hike Route

Pesky Cairn

easy
3.81 mi
+377 ft
Kent Brook Loop

Hike Route

Kent Brook Loop

easy
1.4 mi
+232 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
Oak Ridge to Mount Moosalamoo

Hike Route

Oak Ridge to Mount Moosalamoo

strenuous
12.25 mi
+2,548 ft
Emily Proctor to Cooley Glen Loop

Hike Route

Emily Proctor to Cooley Glen Loop

strenuous
11.55 mi
+3,244 ft
Trail Around Middlebury

Hike Route

Trail Around Middlebury

strenuous
16.24 mi
+1,238 ft
Baker Peak and Griffith Lake

Hike Route

Baker Peak and Griffith Lake

strenuous
10.1 mi
+2,455 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.

Sherburne Loop

Hike Route

Sherburne Loop

strenuous
7.18 mi
+1,866 ft
Pico Peak via Sherburne Pass Trail

Hike Route

Pico Peak via Sherburne Pass Trail

Birding
strenuous
5.41 mi
+1,802 ft
Bucklin Trail to Killington Peak

Hike Route

Bucklin Trail to Killington Peak

strenuous
7.24 mi
+2,481 ft
Killington Loop

Hike Route

Killington Loop

moderate
5.02 mi
+1,785 ft
Chandler Ridge and Leicester Hollow Loop

Hike Route

Chandler Ridge and Leicester Hollow Loop

moderate
9.24 mi
+1,158 ft
Romance Mountain Loop

Hike Route

Romance Mountain Loop

moderate
6.94 mi
+1,282 ft