Hiking trails near Pittsfield, Massachusetts

341 official trails lie within 25 miles of Pittsfield — 788 miles in total, 233 rated easy and 19 hard or expert. Every distance and elevation figure below is computed from the agency centerline and a 10 m elevation model, not crowd-sourced.

The biggest climb nearby gains 2,754 ft; the median trail gains 337 ft.

Open the map on Pittsfield

24 trails worth the drive

Trail	Miles	Climb	Difficulty	From town
Appalachian Trail/Long Trail	11.4	2,754 ft	Expert	14 mi
Appalachian National Scenic Trail	11.4	2,751 ft	Expert	14 mi
Ski Trail	7.2	922 ft	Expert	19 mi
Mahican Mohawk Trail	16.2	1,856 ft	Expert	17 mi
Notchview	16.4	684 ft	Expert	12 mi
Appalachian Trail	8.9	968 ft	Expert	15 mi
Taconic Crest Trail	6.3	1,259 ft	Hard	6 mi
Gould Trail	2.8	1,934 ft	Hard	13 mi
Bellows Pipe Trail	3.1	1,517 ft	Hard	15 mi
Shaker Trail	5.0	693 ft	Hard	4 mi
Money Brook Trail	2.9	1,476 ft	Moderate	15 mi
Taconic Trail	4.3	806 ft	Hard	10 mi
Unnamed trail	1.9	1,638 ft	Moderate	17 mi
Class Of 1933 Trail	1.8	1,473 ft	Moderate	17 mi
Pine Cobble Trail	1.7	1,460 ft	Moderate	18 mi
Phelps Trail	1.8	1,325 ft	Moderate	14 mi
Honwee Loop Trail	3.1	1,038 ft	Moderate	3 mi
Thunderbolt Trail	1.3	1,577 ft	Hard	14 mi
Stony Ledge Ski Trail	1.7	1,369 ft	Moderate	14 mi
Switchback Trail	2.9	860 ft	Moderate	6 mi
Utility Corridor	2.5	1,012 ft	Moderate	6 mi
Haley Farm Trail	1.7	1,325 ft	Moderate	14 mi
Dunbar Brook Trail	3.3	823 ft	Moderate	23 mi
Trout Brook Trail	2.1	1,167 ft	Moderate	21 mi

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