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Hard Hiking Trails near Pittsfield

The directory currently contains 5 quality-checked routes matching this guide near Pittsfield. Their average mapped distance is 51.3 km and average recorded ascent is 1,592 m (5,223 ft); the longest route in the set is 140 km.

This subset represents 10% of the 48 quality-checked routes near Pittsfield. Its average distance is 51.3 km, compared with 8.6 km across the full local set. Average recorded ascent is 1,592 m (5,223 ft), versus 288 m (945 ft) for all quality-checked routes in the same area.

This set contains routes rated hard or expert from their available distance and elevation measurements. Within this set, 0 routes (0%) are rated easy, 5 (100%) are rated hard or expert, and 1 (20%) are recorded as loops. Ratings are computed from available distance and elevation data and do not establish current terrain or access.

Data refreshed September 2026

Choose by the details

How do these routes differ?

A closer look at the first 5 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

13.0 km

Thoreau’s Footsteps

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

Lowest recorded ascent in this sample

705 m

Thoreau’s Footsteps

5 of 5 have ascent data. Missing measurements are excluded.

Return logistics

1 recorded loop

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 →

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.

Trails

Expert

Massachusetts · United States

Distance
140 km
/ 87.2 mi
Elevation gain
3,455 m
Typical duration
38 hr
  • Mountain
  • Waymarked route
  • Long-distance path
Monument atop Mount Greylock at sunset
Hard

Massachusetts · United States

Distance
13.2 km
/ 8.2 mi
Elevation gain
706 m
Typical duration
3 hr 48 min
  • Mountain
  • Summit push
  • Panoramic viewpoint
Expert

Massachusetts · United States

Distance
31.8 km
/ 19.8 mi
Elevation gain
1,253 m
Typical duration
9 hr 1 min
  • Mountain
Expert

Massachusetts · United States

Distance
58.0 km
/ 36.1 mi
Elevation gain
1,841 m
Typical duration
16 hr
  • Mountain
Hard

Massachusetts · United States

Distance
13.0 km
/ 8.1 mi
Elevation gain
705 m
Typical duration
3 hr 46 min

The shortlist, side by side

The ten highest scoring routes on this page, so you can compare effort before opening any of them.

Distance, ascent, walking time and difficulty for the top routes
RouteDistanceAscentTimeDifficultyBest season
Appalachian TrailMassachusetts140 km3,455 m38 hrExpertApril to October
Jones Nose to SummitMassachusetts13.2 km706 m3 hr 48 minHardApril to October
Mahican-Mohawk Trail (M-M)Massachusetts31.8 km1,253 m9 hr 1 minExpertApril to October
Taconic Crest TrailMassachusetts58.0 km1,841 m16 hrExpertApril to October
Thoreau’s FootstepsMassachusetts13.0 km705 m3 hr 46 minHardApril to October

Appalachian Trail, Jones Nose to Summit, Mahican-Mohawk Trail (M-M) currently rank highest in this filtered set according to the directory score. Open an individual route to inspect its mapped line, elevation profile, data source and planning caveats. Check live access, conditions and local rules with an official source before travelling.

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