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Massachusetts, United States

Hiking trails near Pittsfield

48 quality-checked hiking routes are currently mapped within 40 km of Pittsfield, Massachusetts, United States. Together their route lines cover 413 km. The average route is 8.6 km with 288 m (945 ft) of recorded ascent.

48
Trails
40 km
Search radius
17
Easy routes
0.5 km
Closest

The directory difficulty mix is 17 easy (35%), 26 moderate (54%) and 5 hard or expert (11%). 7 routes (15%) are recorded as loops. Difficulty is calculated from available distance and elevation data; it is not a statement about technical terrain or current conditions.

The most frequent route tags are mountain (9), river (3), panoramic viewpoint (3), summit push (2). The highest recorded point in this set is 1,063 m (3,488 ft). The place-level planning field lists varies by region as the preferred season; check each route and official notices for live access and weather. Appalachian Trail, Jones Nose to Summit, Mahican-Mohawk Trail (M-M) currently lead this page’s directory ranking, which uses route completeness and computed route scores rather than editorial field testing.

Choose by the details

How do these routes differ?

A closer look at the first 6 routes in this page’s default ordering. These comparisons describe this sample, not the entire destination or a field-tested recommendation.

Shortest mapped distance in this sample

1.4 km

Simon's Rock Interpretive Trail

Compare the climbing too; shortest does not necessarily mean easiest.

Lowest recorded ascent in this sample

51 m

Simon's Rock Interpretive Trail

6 of 6 have ascent data. Missing measurements are excluded.

Return logistics

0 recorded loops

Check start and finish for every option. An unknown shape does not mean a loop, and a loop does not establish access to its start.

Plan the return journey →
Comparison of the first 6 listed routes
RouteDistanceAscentMoving timeShape
Appalachian Trail140 km3,455 m38 hrPoint to point
Jones Nose to Summit13.2 km706 m3 hr 48 minPoint to point
Mahican-Mohawk Trail (M-M)31.8 km1,253 m9 hr 1 minPoint to point
Cheshire Harbor Trail2.0 km159 m39 minPoint to point
Simon's Rock Interpretive Trail1.4 km51 m22 minPoint to point
Wilbur’s Clearing to Summit9.1 km626 m2 hr 50 minPoint to point

Distances follow stored route lines; ascent and time are estimates. Current access, surface and technical difficulty need separate checks. How to turn a comparison into a shortlist.

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