A bird sitting on a nest of eggs.

Hiking Near Hinsdale, 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.

Canoe Meadows Wildlife Sanctuary Trail

Hike Route

Canoe Meadows Wildlife Sanctuary Trail

Birding
easy
2.64 mi
+41 ft
Washington Mountain Marsh

Hike Route

Washington Mountain Marsh

Birding
easy
3.19 mi
+163 ft
Notchview Reservation Circuit Trail

Hike Route

Notchview Reservation Circuit Trail

Family Friendly
easy
1.82 mi
+137 ft
Gorge Trail to Felton Pond

Hike Route

Gorge Trail to Felton Pond

Lake
easy
1.73 mi
+594 ft
Bradley Farm Trail

Hike Route

Bradley Farm Trail

Historical
easy
2.08 mi
+469 ft
Ledges/Overbrook Loop

Hike Route

Ledges/Overbrook Loop

Birding
strenuous
2.37 mi
+906 ft
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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.

Greylock in the Round

Hike Route

Greylock in the Round

Historical
strenuous
11.51 mi
+3,016 ft
Long Trail to Lake Hancock

Hike Route

Long Trail to Lake Hancock

strenuous
12.3 mi
+2,292 ft
Robert Frost Trail

Hike Route

Robert Frost Trail

Birding
strenuous
43.37 mi
+7,005 ft
Long Trail to Glastenbury Lookout

Hike Route

Long Trail to Glastenbury Lookout

extreme
19.05 mi
+4,561 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.

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
Mount Greylock Summit Loop

Hike Route

Mount Greylock Summit Loop

Fall Colors
strenuous
6.37 mi
+2,283 ft
Bellows Pipe to Mt Greylock Summit

Hike Route

Bellows Pipe to Mt Greylock Summit

Commonly Backpacked
strenuous
5.67 mi
+2,253 ft
Spruce Mountain Trail

Hike Route

Spruce Mountain Trail

Scenic
moderate
6.17 mi
+1,251 ft
Cherry Plain Loop

Hike Route

Cherry Plain Loop

moderate
7.39 mi
+798 ft
Broad Brook to Seth Warner Shelter

Hike Route

Broad Brook to Seth Warner Shelter

strenuous
8.22 mi
+1,436 ft