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Hiking Trails Under 5 km near Pittsfield

The directory currently contains 36 quality-checked routes matching this guide near Pittsfield. Their average mapped distance is 2.8 km and average recorded ascent is 105 m (344 ft); the longest route in the set is 5.0 km.

This subset represents 75% of the 48 quality-checked routes near Pittsfield. Its average distance is 2.8 km, compared with 8.6 km across the full local set. Average recorded ascent is 105 m (344 ft), versus 288 m (945 ft) for all quality-checked routes in the same area.

Every route in this set has a mapped distance of 5 km or less. Time and suitability still depend on ascent, surface and conditions. Within this set, 16 routes (44%) are rated easy, 0 (0%) are rated hard or expert, and 5 (14%) 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 Trail

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

Lowest recorded ascent in this sample

0 m

Downtown Loop

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 →

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

Cheshire Harbor Trail

Massachusetts · United States

Distance
2.0 km
/ 1.2 mi
Elevation gain
159 m
Typical duration
39 min
  • Mountain
  • Panoramic viewpoint
Easy

Clam River Loop

Massachusetts · United States

Distance
2.2 km
/ 1.4 mi
Elevation gain
52 m
Typical duration
32 min
  • River
Easy

Downtown Loop

Massachusetts · United States

Distance
3.3 km
/ 2.0 mi
Typical duration
41 min
Moderate

Eagle Ledge Trail

Massachusetts · United States

Distance
2.7 km
/ 1.7 mi
Elevation gain
165 m
Typical duration
48 min
  • Forest
Moderate

Charcol Trail

Massachusetts · United States

Distance
2.8 km
/ 1.7 mi
Elevation gain
160 m
Typical duration
50 min
Easy

Clam River Trail

Massachusetts · United States

Distance
2.7 km
/ 1.7 mi
Elevation gain
112 m
Typical duration
43 min
  • River
Moderate

Hickey and Peeskawso Loop

Massachusetts · United States

Distance
3.9 km
/ 2.4 mi
Elevation gain
271 m
Typical duration
1 hr 13 min
Moderate

Blue Trail

Massachusetts · United States

Distance
3.2 km
/ 2.0 mi
Elevation gain
99 m
Typical duration
49 min
Easy

Orange Trail

Massachusetts · United States

Distance
0.5 km
/ 0.3 mi
Typical duration
7 min
Easy

Yellow Trail

Massachusetts · United States

Distance
2.4 km
/ 1.5 mi
Elevation gain
63 m
Typical duration
35 min
Moderate

Hoosic Ridge Trail

Massachusetts · United States

Distance
4.0 km
/ 2.5 mi
Elevation gain
209 m
Typical duration
1 hr 8 min
  • Mountain
Easy

Hammertown Loop

Massachusetts · United States

Distance
2.7 km
/ 1.7 mi
Elevation gain
62 m
Typical duration
40 min
Moderate

Dunbar Brook Trail

Massachusetts · United States

Distance
4.9 km
/ 3.0 mi
Elevation gain
294 m
Typical duration
1 hr 27 min
  • River
Moderate

Indian Trail

Massachusetts · United States

Distance
1.2 km
/ 0.8 mi
Elevation gain
281 m
Typical duration
41 min
Moderate

Busby Trail

Massachusetts · United States

Distance
1.9 km
/ 1.2 mi
Typical duration
23 min
Moderate

North Pond Loop

Massachusetts · United States

Distance
3.9 km
/ 2.4 mi
Elevation gain
99 m
Typical duration
58 min
Easy

Stony Ledge

Massachusetts · United States

Distance
2.8 km
/ 1.7 mi
Elevation gain
62 m
Typical duration
40 min
Moderate

Switchback Trail

Massachusetts · United States

Distance
3.8 km
/ 2.3 mi
Elevation gain
290 m
Typical duration
1 hr 13 min
Moderate

Boulder Trail

Massachusetts · United States

Distance
4.3 km
/ 2.7 mi
Elevation gain
122 m
Typical duration
1 hr 5 min
Moderate

Schemerhorn Trail

Massachusetts · United States

Distance
2.7 km
/ 1.7 mi
Elevation gain
190 m
Typical duration
51 min
Moderate

Totem Trail

Massachusetts · United States

Distance
1.6 km
/ 1.0 mi
Elevation gain
33 m
Typical duration
23 min
Easy

Aqueduct Trail

Massachusetts · United States

Distance
3.5 km
/ 2.1 mi
Typical duration
43 min
Easy

Ashley Trail

Massachusetts · United States

Distance
2.3 km
/ 1.4 mi
Elevation gain
59 m
Typical duration
34 min
Easy

Basin Pond Trail

Massachusetts · United States

Distance
3.5 km
/ 2.1 mi
Elevation gain
110 m
Typical duration
53 min
Moderate

Buckley Dunton Trail

Massachusetts · United States

Distance
3.5 km
/ 2.1 mi
Elevation gain
41 m
Typical duration
47 min
Easy

Felton Trail

Massachusetts · United States

Distance
2.9 km
/ 1.8 mi
Elevation gain
60 m
Typical duration
41 min
Easy

Mother Loop Trail

Massachusetts · United States

Distance
3.8 km
/ 2.4 mi
Elevation gain
73 m
Typical duration
54 min
Easy

Navin Trail

Massachusetts · United States

Distance
1.8 km
/ 1.1 mi
Elevation gain
64 m
Typical duration
28 min
Easy

Spruce Trail

Massachusetts · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
42 m
Typical duration
22 min
Moderate

Stevens Glenn Loop Trail

Massachusetts · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
109 m
Typical duration
26 min
Easy

Old Mill Trail

Massachusetts · United States

Distance
2.3 km
/ 1.4 mi
Elevation gain
49 m
Typical duration
33 min
Easy

Tyler Swamp Loop

Massachusetts · United States

Distance
3.5 km
/ 2.1 mi
Elevation gain
52 m
Typical duration
48 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
Cheshire Harbor TrailMassachusetts2.0 km159 m39 minModerateApril to October
Simon's Rock Interpretive TrailMassachusetts1.4 km51 m22 minModerateApril to October
Clam River LoopMassachusetts2.2 km52 m32 minEasyApril to October
Keystone Arch Bridges TrailMassachusetts3.5 km100 m53 minModerateApril to October
Downtown LoopMassachusetts3.3 km0 m41 minEasyApril to October
Eagle Ledge TrailMassachusetts2.7 km165 m48 minModerateApril to October
Charcol TrailMassachusetts2.8 km160 m50 minModerateApril to October
Clam River TrailMassachusetts2.7 km112 m43 minEasyApril to October
Hickey and Peeskawso LoopMassachusetts3.9 km271 m1 hr 13 minModerateApril to October
Blue TrailMassachusetts3.2 km99 m49 minModerateApril to October

Cheshire Harbor Trail, Simon's Rock Interpretive Trail, Downtown Loop 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

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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.

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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.

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