A bird sitting on a nest of eggs.

Hiking Near Lee, 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.

Gorge Trail to Felton Pond

Hike Route

Gorge Trail to Felton Pond

Lake
easy
1.73 mi
+594 ft
Washington Mountain Marsh

Hike Route

Washington Mountain Marsh

Birding
easy
3.19 mi
+163 ft
Ledges/Overbrook Loop

Hike Route

Ledges/Overbrook Loop

Birding
strenuous
2.37 mi
+906 ft
Peeskawso Peak Loop

Hike Route

Peeskawso Peak Loop

Birding
easy
2.43 mi
+751 ft
Flag Rock

Hike Route

Flag Rock

Birding
moderate
3.55 mi
+820 ft
Lookout Trail to Vista View

Hike Route

Lookout Trail to Vista View

Fall Colors
easy
2.68 mi
+316 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.

Greylock in the Round

Hike Route

Greylock in the Round

Historical
strenuous
11.51 mi
+3,016 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
Bear Mountain

Hike Route

Bear Mountain

Birding
moderate
5.23 mi
+1,555 ft
Mount Greylock Summit Loop

Hike Route

Mount Greylock Summit Loop

Fall Colors
strenuous
6.37 mi
+2,283 ft
Halfway Brook-Hubbard River Trails

Hike Route

Halfway Brook-Hubbard River Trails

Historical
easy
5.08 mi
+508 ft
Cherry Plain Loop

Hike Route

Cherry Plain Loop

moderate
7.39 mi
+798 ft
Bellows Pipe to Mt Greylock Summit

Hike Route

Bellows Pipe to Mt Greylock Summit

Commonly Backpacked
strenuous
5.67 mi
+2,253 ft