The best running trails in Berkshire County
4.5
(2)
380
runners
87
runs
Last updated: October 2, 2025
1
runners
1. Stony Ledge Trail – Mount Greylock State Park
5.30km
00:36
140m
140m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2. Finerty Pond Trail – October Mountain State Park
4.38km
00:34
100m
100m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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3. Honwee Loop Trail – Pittsfield State Forest
5.22km
00:49
310m
310m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5. Flat Rock Hill Trail – Savoy Mountain State Forest
5.20km
00:41
140m
140m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
16
runners
6. Running loop from Williamstown
6.50km
00:42
60m
60m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
12
runners
7. Cheshire Reservoir loop from Pittsfield
17.5km
01:48
30m
30m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
11
runners
8. Stony Ledge loop from Williamstown
19.7km
02:59
960m
960m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
15
runners
9. Interlacken Common – Kripalu Yoga Fellowship loop from Lenox
11.2km
01:11
140m
140m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
15
runners
10. Interlacken Common – Kripalu Yoga Fellowship loop from West Stockbridge
11.1km
01:10
140m
140m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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