Hiking TrailsUnited States of AmericaNew Marlborough, Massachusetts

Hiking Trails
Near New Marlborough, Massachusetts

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.

Mount Frissell and Tri-State Marker

Classic Hike Route

Mount Frissell and Tri-State Marker

Dogs Allowed
moderate
3.06 mi
+1,176 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.

Leffingwell Loop

Hike Route

Leffingwell Loop

Birding
easy
2.32 mi
+383 ft
York Lake Loop Trail

Hike Route

York Lake Loop Trail

Birding
easy
2.27 mi
+64 ft
Lookout Trail to Vista View

Hike Route

Lookout Trail to Vista View

Fall Colors
easy
2.68 mi
+316 ft
Benedict Pond Loop

Hike Route

Benedict Pond Loop

Lake
easy
1.7 mi
+65 ft
Lime Kiln Farm Wildlife Sanctuary Loop

Hike Route

Lime Kiln Farm Wildlife Sanctuary Loop

Birding
easy
2.13 mi
+177 ft
Bartholomew's Cobble Trail

Hike Route

Bartholomew's Cobble Trail

River/Creek
easy
3.55 mi
+510 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.

Bear Mountain

Hike Route

Bear Mountain

Birding
moderate
5.23 mi
+1,555 ft
Rand's View Out and Back

Hike Route

Rand's View Out and Back

Fall Colors
strenuous
5.25 mi
+1,323 ft
Halfway Brook-Hubbard River Trails

Hike Route

Halfway Brook-Hubbard River Trails

Historical
easy
5.08 mi
+508 ft
Kite Hill-Fox HIll and Charcoal Loop

Hike Route

Kite Hill-Fox HIll and Charcoal Loop

moderate
5.24 mi
+584 ft
Ashuwillticook Rail Trail - Berkshire Mall Road to the town of Cheshire

Hike Route

Ashuwillticook Rail Trail - Berkshire Mall Road to the town of Cheshire

Dogs Allowed
easy
5.77 mi
+1 ft
Macedonia Ridge Trail

Hike Route

Macedonia Ridge Trail

Views
strenuous
6.39 mi
+1,788 ft