The best running trails around Pittsfield
5.0
(1)
77
runners
20
runs
Last updated: September 15, 2025
1. Honwee Loop Trail – Pittsfield State Forest
5.22km
00:49
310m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
12
runners
2. Cheshire Reservoir loop from Pittsfield
17.5km
01:48
30m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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6
runners
3. Under Mountain Rest loop from Lenox
7.86km
00:50
110m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
runners
4. View to west loop from Lenox
8.85km
01:04
220m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
runners
5. Holl-Fox Reserve loop from Lenox
7.39km
00:47
110m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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