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
Lookout Trail to Vista View

Hike Route

Lookout Trail to Vista View

Fall Colors
unknown
2.68 mi
+316 ft
Sanderson Brook Falls Trail

Hike Route

Sanderson Brook Falls Trail

River/Creek
moderate
1.95 mi
+307 ft
Jug End Loop Trail

Hike Route

Jug End Loop Trail

Birding
moderate
2.94 mi
+345 ft
Lion's Head

Hike Route

Lion's Head

Views
easy
1.09 mi
+571 ft
CT State Highpoint/Tri-point Out and Back

Hike Route

CT State Highpoint/Tri-point Out and Back

Geologically Significant
strenuous
3.06 mi
+1,155 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.

Rand's View Out and Back

Hike Route

Rand's View Out and Back

Fall Colors
strenuous
5.25 mi
+1,201 ft
Bear Mountain

Hike Route

Bear Mountain

Birding
moderate
5.23 mi
+1,560 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
Heublein Tower from Reservoir 6

Hike Route

Heublein Tower from Reservoir 6

Views
moderate
6.29 mi
+608 ft
Macedonia Ridge Trail

Hike Route

Macedonia Ridge Trail

Views
strenuous
6.39 mi
+1,788 ft