Hiking TrailsUnited States of AmericaChimney Hill, Vermont

Hiking Trails
Near Chimney Hill, 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 2)

Classic Hike Route

The Long Trail (Division 2)

Birding
strenuous
21.04 mi
+4,994 ft
The Long Trail (Division 3)

Classic Hike Route

The Long Trail (Division 3)

Birding
strenuous
21.5 mi
+4,411 ft
The Long Trail (Division 1)

Classic Hike Route

The Long Trail (Division 1)

Birding
moderate
13.34 mi
+2,498 ft
The Long Trail (Division 4)

Classic Hike Route

The Long Trail (Division 4)

Birding
strenuous
19.67 mi
+3,325 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.

Haystack Mountain (Wilmington)

Hike Route

Haystack Mountain (Wilmington)

moderate
4.1 mi
+1,042 ft
Mt Olga Loop

Hike Route

Mt Olga Loop

easy
1.57 mi
+549 ft
Hogback Mountain

Hike Route

Hogback Mountain

easy
2.4 mi
+264 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
1.37 mi
+598 ft
Prospect Ski Area Loop

Hike Route

Prospect Ski Area Loop

easy
1.6 mi
+601 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.

Haystack Mountain and Mount Snow

Hike Route

Haystack Mountain and Mount Snow

strenuous
11.64 mi
+2,406 ft
Long Trail to Glastenbury Lookout

Hike Route

Long Trail to Glastenbury Lookout

extreme
19.05 mi
+4,563 ft
The Long Trail (Division 2)

Classic Hike Route

The Long Trail (Division 2)

Birding
strenuous
21.04 mi
+4,994 ft
West Ridge to Glastenbury Lookout

Hike Route

West Ridge to Glastenbury Lookout

extreme
18.39 mi
+4,362 ft
Stratton Mountain and Pond

Hike Route

Stratton Mountain and Pond

strenuous
11.07 mi
+2,184 ft
The Long Trail (Division 3)

Classic Hike Route

The Long Trail (Division 3)

Birding
strenuous
21.5 mi
+4,411 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
+1,985 ft
Little Pond

Hike Route

Little Pond

easy
5.12 mi
+469 ft
Spruce Mountain Trail

Hike Route

Spruce Mountain Trail

Scenic
moderate
6.17 mi
+1,251 ft
Long Trail to Stratton Mountain

Hike Route

Long Trail to Stratton Mountain

strenuous
6.92 mi
+1,763 ft
Dunbar Brook Trail

Hike Route

Dunbar Brook Trail

River/Creek
strenuous
6.02 mi
+1,106 ft
Stratton Pond

Hike Route

Stratton Pond

moderate
8.23 mi
+723 ft