The best running trails around Cheshire
29
runners
5
runs
Last updated: September 13, 2025
1
runners
1. Stony Ledge Trail – Mount Greylock State Park
5.30km
00:36
140m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
runners
2. Mount Greylock loop from Adams
8.33km
01:31
680m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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6
runners
3. Mount Greylock – Greylock Glen loop from Adams
11.3km
01:49
680m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
runners
4. Cheshire Reservoir – Berkshire Pond loop from Cheshire
41.2km
04:16
180m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
runners
5. Mount Greylock – Jones Nose loop from Adams
20.8km
03:00
820m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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