Hiking TrailsUnited States of AmericaPittsford, Vermont

Hiking Trails
Near Pittsford, Vermont

Regional Classics Icon

Regional Classics

Discover the must-do hikes in the area, handpicked and curated by local experts who know the trails best. These routes are beloved for good reason, offering standout scenery, rewarding terrain, and detailed descriptions with tips that tell you exactly what to expect. Whether you are visiting for the first time or are a local doing them on repeat, they offer a reliable and memorable hiking experience.

The Long Trail (Division 6)

Classic Hike Route

The Long Trail (Division 6)

Birding
moderate
19.55 mi
+3,600 ft
The Long Trail (Division 7)

Classic Hike Route

The Long Trail (Division 7)

Birding
strenuous
20.85 mi
+6,698 ft
The Long Trail (Division 5)

Classic Hike Route

The Long Trail (Division 5)

Birding
strenuous
22.7 mi
+6,218 ft
The Long Trail (Division 8)

Classic Hike Route

The Long Trail (Division 8)

Birding
strenuous
17.28 mi
+4,679 ft
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.

Falls Trail

Hike Route

Falls Trail

easy
2.44 mi
+461 ft
Taconic Mountains Ramble Loop

Hike Route

Taconic Mountains Ramble Loop

easy
1.38 mi
+457 ft
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
High Pond

Hike Route

High Pond

easy
3.98 mi
+542 ft
Half Moon Pond

Hike Route

Half Moon Pond

easy
1.12 mi
+18 ft
Logo

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.

The Long Trail (Division 6)

Classic Hike Route

The Long Trail (Division 6)

Birding
moderate
19.55 mi
+3,600 ft
The Long Trail (Division 7)

Classic Hike Route

The Long Trail (Division 7)

Birding
strenuous
20.85 mi
+6,698 ft
The Long Trail (Division 5)

Classic Hike Route

The Long Trail (Division 5)

Birding
strenuous
22.7 mi
+6,218 ft
Oak Ridge to Mount Moosalamoo

Hike Route

Oak Ridge to Mount Moosalamoo

strenuous
12.25 mi
+2,546 ft
Trail Around Middlebury

Hike Route

Trail Around Middlebury

strenuous
16.24 mi
+1,261 ft
Emily Proctor to Cooley Glen Loop

Hike Route

Emily Proctor to Cooley Glen Loop

strenuous
11.55 mi
+3,244 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.

Chandler Ridge and Leicester Hollow Loop

Hike Route

Chandler Ridge and Leicester Hollow Loop

moderate
9.24 mi
+1,158 ft
Bucklin Trail to Killington Peak

Hike Route

Bucklin Trail to Killington Peak

strenuous
7.24 mi
+2,472 ft
Pico Peak via Sherburne Pass Trail

Hike Route

Pico Peak via Sherburne Pass Trail

Birding
strenuous
5.41 mi
+1,804 ft
Sherburne Loop

Hike Route

Sherburne Loop

strenuous
7.18 mi
+1,866 ft
Glen Lake Ponds Trail

Hike Route

Glen Lake Ponds Trail

moderate
8.41 mi
+870 ft
Romance Mountain Loop

Hike Route

Romance Mountain Loop

moderate
6.94 mi
+1,282 ft