A bird sitting on a nest of eggs.

Hiking Near Conway, 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.

Chapel Ledge

Hike Route

Chapel Ledge

River/Creek
easy
0.75 mi
+262 ft
Fire Tower Loop Hike

Hike Route

Fire Tower Loop Hike

Boat Ramp
easy
3.14 mi
+329 ft
Long Trail to Hemlock Trail

Hike Route

Long Trail to Hemlock Trail

Boat Ramp
easy
1.62 mi
+50 ft
Shelburne Falls Fire Tower Trail

Hike Route

Shelburne Falls Fire Tower Trail

Historical
easy
2.5 mi
+1,051 ft
Graves Farm Wildlife Sanctuary Loop

Hike Route

Graves Farm Wildlife Sanctuary Loop

Birding
easy
1.35 mi
+88 ft
High Ledges Wildlife Sanctuary Loop

Hike Route

High Ledges Wildlife Sanctuary Loop

Birding
easy
3.25 mi
+728 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.

Robert Frost Trail

Hike Route

Robert Frost Trail

Birding
strenuous
43.37 mi
+7,005 ft
Northfield Mountain Trails

Hike Route

Northfield Mountain Trails

Cave
strenuous
11 mi
+2,200 ft
Greylock in the Round

Hike Route

Greylock in the Round

Historical
strenuous
11.51 mi
+3,016 ft
Haystack Mountain and Mount Snow

Hike Route

Haystack Mountain and Mount Snow

strenuous
11.64 mi
+2,406 ft
Long Trail to Lake Hancock

Hike Route

Long Trail to Lake Hancock

strenuous
12.3 mi
+2,292 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.

Leyden Blueberry Fields

Hike Route

Leyden Blueberry Fields

Birding
moderate
5.5 mi
+995 ft
Spruce Mountain Trail

Hike Route

Spruce Mountain Trail

Scenic
moderate
6.17 mi
+1,251 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
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
Corridor 9 to Dome Mountain

Hike Route

Corridor 9 to Dome Mountain

strenuous
8.35 mi
+1,984 ft