Moderate
Massachusetts · United States
- Distance
- 2.0 km / 1.2 mi
- Elevation gain
- 159 m
- Typical duration
- 39 min
- Mountain
- Panoramic viewpoint
Moderate Hiking Trails near Pittsfield
The directory currently contains 26 quality-checked routes matching this guide near Pittsfield. Their average mapped distance is 4.2 km and average recorded ascent is 192 m (630 ft); the longest route in the set is 11.4 km.
This subset represents 54% of the 48 quality-checked routes near Pittsfield. Its average distance is 4.2 km, compared with 8.6 km across the full local set. Average recorded ascent is 192 m (630 ft), versus 288 m (945 ft) for all quality-checked routes in the same area.
Every route in this set is rated moderate by the directory’s distance-and-elevation model. Technical terrain and live conditions are not part of that rating. Within this set, 0 routes (0%) are rated easy, 0 (0%) are rated hard or expert, and 3 (12%) 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 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 TrailCompare the climbing too; shortest does not necessarily mean easiest.
Lowest recorded ascent in this sample
51 m
Simon's Rock Interpretive Trail6 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 →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
Moderate
Massachusetts · United States
- Distance
- 1.4 km / 0.9 mi
- Elevation gain
- 51 m
- Typical duration
- 22 min
- Waymarked route
Moderate
Massachusetts · United States
- Distance
- 9.1 km / 5.6 mi
- Elevation gain
- 626 m
- Typical duration
- 2 hr 50 min
- Mountain
- Summit push
- Panoramic viewpoint
Moderate
Massachusetts · United States
- Distance
- 3.5 km / 2.2 mi
- Elevation gain
- 100 m
- Typical duration
- 53 min
Moderate
Massachusetts · United States
- Distance
- 5.5 km / 3.4 mi
- Elevation gain
- 314 m
- Typical duration
- 1 hr 37 min
Moderate
Massachusetts · United States
- Distance
- 2.7 km / 1.7 mi
- Elevation gain
- 165 m
- Typical duration
- 48 min
- Forest
Moderate
Massachusetts · United States
- Distance
- 2.8 km / 1.7 mi
- Elevation gain
- 160 m
- Typical duration
- 50 min
Moderate
Massachusetts · United States
- Distance
- 3.9 km / 2.4 mi
- Elevation gain
- 271 m
- Typical duration
- 1 hr 13 min
Moderate
Massachusetts · United States
- Distance
- 3.2 km / 2.0 mi
- Elevation gain
- 99 m
- Typical duration
- 49 min
Moderate
Massachusetts · United States
- Distance
- 3.7 km / 2.3 mi
- Elevation gain
- 149 m
- Typical duration
- 59 min
Moderate
Massachusetts · United States
- Distance
- 10.5 km / 6.5 mi
- Elevation gain
- 430 m
- Typical duration
- 2 hr 50 min
- Mountain
Moderate
Massachusetts · United States
- Distance
- 4.0 km / 2.5 mi
- Elevation gain
- 209 m
- Typical duration
- 1 hr 8 min
- Mountain
Moderate
Massachusetts · United States
- Distance
- 5.0 km / 3.1 mi
- Elevation gain
- 84 m
- Typical duration
- 1 hr 10 min
- Mountain
Moderate
Massachusetts · United States
- Distance
- 4.9 km / 3.0 mi
- Elevation gain
- 294 m
- Typical duration
- 1 hr 27 min
- River
Moderate
Massachusetts · United States
- Distance
- 1.2 km / 0.8 mi
- Elevation gain
- 281 m
- Typical duration
- 41 min
Moderate
Massachusetts · United States
- Distance
- 11.4 km / 7.1 mi
- Elevation gain
- 319 m
- Typical duration
- 2 hr 51 min
Moderate
Moderate
Massachusetts · United States
- Distance
- 3.9 km / 2.4 mi
- Elevation gain
- 99 m
- Typical duration
- 58 min
Moderate
Massachusetts · United States
- Distance
- 6.2 km / 3.8 mi
- Elevation gain
- 163 m
- Typical duration
- 1 hr 32 min
Moderate
Massachusetts · United States
- Distance
- 3.8 km / 2.3 mi
- Elevation gain
- 290 m
- Typical duration
- 1 hr 13 min
Moderate
Massachusetts · United States
- Distance
- 4.3 km / 2.7 mi
- Elevation gain
- 122 m
- Typical duration
- 1 hr 5 min
Moderate
Massachusetts · United States
- Distance
- 5.8 km / 3.6 mi
- Elevation gain
- 244 m
- Typical duration
- 1 hr 34 min
Moderate
Massachusetts · United States
- Distance
- 2.7 km / 1.7 mi
- Elevation gain
- 190 m
- Typical duration
- 51 min
Moderate
Massachusetts · United States
- Distance
- 1.6 km / 1.0 mi
- Elevation gain
- 33 m
- Typical duration
- 23 min
Moderate
Massachusetts · United States
- Distance
- 3.5 km / 2.1 mi
- Elevation gain
- 41 m
- Typical duration
- 47 min
Moderate
Massachusetts · United States
- Distance
- 1.3 km / 0.8 mi
- Elevation gain
- 109 m
- Typical duration
- 26 min
The shortlist, side by side
The ten highest scoring routes on this page, so you can compare effort before opening any of them.
| Route | Distance | Ascent | Time | Difficulty | Best season |
|---|---|---|---|---|---|
| Cheshire Harbor TrailMassachusetts | 2.0 km | 159 m | 39 min | Moderate | April to October |
| Simon's Rock Interpretive TrailMassachusetts | 1.4 km | 51 m | 22 min | Moderate | April to October |
| Wilbur’s Clearing to SummitMassachusetts | 9.1 km | 626 m | 2 hr 50 min | Moderate | April to October |
| Keystone Arch Bridges TrailMassachusetts | 3.5 km | 100 m | 53 min | Moderate | April to October |
| Burbank TrailMassachusetts | 5.5 km | 314 m | 1 hr 37 min | Moderate | April to October |
| Eagle Ledge TrailMassachusetts | 2.7 km | 165 m | 48 min | Moderate | April to October |
| Charcol TrailMassachusetts | 2.8 km | 160 m | 50 min | Moderate | April to October |
| Hickey and Peeskawso LoopMassachusetts | 3.9 km | 271 m | 1 hr 13 min | Moderate | April to October |
| Blue TrailMassachusetts | 3.2 km | 99 m | 49 min | Moderate | April to October |
| Rounds Rock - Jones Nose LoopMassachusetts | 3.7 km | 149 m | 59 min | Moderate | April to October |
Cheshire Harbor Trail, Simon's Rock Interpretive Trail, Wilbur’s Clearing to Summit 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.
Frequently asked questions
Plan with more confidence
All planning articles →Choosing a route
How to choose a hike beyond the difficulty label
Compare distance, climbing, route shape and missing information to build a shortlist that fits your day.
Read article →Understanding the map
Read an elevation profile without misreading the climb
Understand total ascent, net height change, profile scale and the section breakdown on each mapped route.
Read article →Planning your day
Build a hiking time plan with room for your own pace
Separate moving time, climbing allowance and stops, then explore how changing your assumptions changes the plan.
Read article →Related guides
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