A bird sitting on a nest of eggs.

Hiking Near Sandisfield, Massachusetts

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.

York Lake Loop Trail

Hike Route

York Lake Loop Trail

Birding
easy
2.27 mi
+64 ft
Richardson Brook Wildlife Sanctuary Loop

Hike Route

Richardson Brook Wildlife Sanctuary Loop

Geologically Significant
easy
1.51 mi
+291 ft
Leffingwell Loop

Hike Route

Leffingwell Loop

Birding
easy
2.32 mi
+383 ft
Old Baldy Summit Trail

Hike Route

Old Baldy Summit Trail

Birding
easy
0.54 mi
+137 ft
Ordway-Searles-Sattler Loop

Hike Route

Ordway-Searles-Sattler Loop

Historical
easy
3.65 mi
+289 ft
Healthy Heart Loop

Hike Route

Healthy Heart Loop

easy
1.41 mi
+55 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.

Halfway Brook-Hubbard River Trails

Hike Route

Halfway Brook-Hubbard River Trails

Historical
easy
5.08 mi
+508 ft
Rand's View Out and Back

Hike Route

Rand's View Out and Back

Fall Colors
strenuous
5.25 mi
+1,323 ft
Bear Mountain

Hike Route

Bear Mountain

Birding
moderate
5.23 mi
+1,555 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
+0 ft
Heublein Tower from Reservoir 6

Hike Route

Heublein Tower from Reservoir 6

Views
moderate
6.29 mi
+608 ft