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
Hard Hiking Trails in Massachusetts
The directory currently contains 34 quality-checked routes matching this guide in Massachusetts. Their average mapped distance is 50.3 km and average recorded ascent is 618 m (2,028 ft); the longest route in the set is 381 km.
This subset represents 11% of the 300 quality-checked routes in Massachusetts. Its average distance is 50.3 km, compared with 9.0 km across the full local set. Average recorded ascent is 618 m (2,028 ft), versus 124 m (407 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, 34 (100%) are rated hard or expert, and 2 (6%) 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
13.2 km
Jones Nose to SummitCompare the climbing too; shortest does not necessarily mean easiest.
Lowest recorded ascent in this sample
706 m
Jones Nose to Summit6 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
Expert
Massachusetts · United States
- Distance
- 150 km / 93.2 mi
- Elevation gain
- 1,611 m
- Typical duration
- 37 hr
- Mountain
- Waymarked route
- Long-distance path
Expert
Massachusetts · United States
- Distance
- 30.0 km / 18.7 mi
- Elevation gain
- 1,346 m
- Typical duration
- 8 hr 43 min
- Mountain
- Waymarked route
Expert
Massachusetts · United States
- Distance
- 33.3 km / 20.7 mi
- Elevation gain
- 1,278 m
- Typical duration
- 9 hr 24 min
- Mountain
- Waymarked route
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
- 68.4 km / 42.5 mi
- Elevation gain
- 1,504 m
- Typical duration
- 18 hr
- Mountain
- Waymarked route
- Long-distance path
Expert
Massachusetts · United States
- Distance
- 381 km / 237 mi
- Elevation gain
- 774 m
- Typical duration
- 91 hr
- Mountain
- Long-distance path
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
- 50.9 km / 31.6 mi
- Elevation gain
- 508 m
- Typical duration
- 12 hr
- Mountain
Expert
Massachusetts · United States
- Distance
- 35.7 km / 22.2 mi
- Elevation gain
- 684 m
- Typical duration
- 9 hr 6 min
- Mountain
Expert
Massachusetts · United States
- Distance
- 44.8 km / 27.9 mi
- Elevation gain
- 210 m
- Typical duration
- 10 hr
- Mountain
Expert
Massachusetts · United States
- Distance
- 40.4 km / 25.1 mi
- Elevation gain
- 309 m
- Typical duration
- 9 hr 39 min
- Mountain
Hard
Massachusetts · United States
- Distance
- 14.9 km / 9.3 mi
- Elevation gain
- 699 m
- Typical duration
- 4 hr 9 min
- Waymarked route
Hard
Massachusetts · United States
- Distance
- 32.2 km / 20.0 mi
- Elevation gain
- 281 m
- Typical duration
- 7 hr 38 min
Hard
Massachusetts · United States
- Distance
- 23.8 km / 14.8 mi
- Elevation gain
- 70 m
- Typical duration
- 5 hr 20 min
Hard
Massachusetts · United States
- Distance
- 25.4 km / 15.8 mi
- Elevation gain
- 154 m
- Typical duration
- 5 hr 50 min
Hard
Massachusetts · United States
- Distance
- 20.2 km / 12.6 mi
- Elevation gain
- 82 m
- Typical duration
- 4 hr 30 min
Hard
Massachusetts · United States
- Distance
- 31.4 km / 19.5 mi
- Elevation gain
- 199 m
- Typical duration
- 7 hr 21 min
Hard
Massachusetts · United States
- Distance
- 21.8 km / 13.6 mi
- Elevation gain
- 175 m
- Typical duration
- 5 hr 1 min
Expert
Massachusetts · United States
- Distance
- 46.0 km / 28.6 mi
- Elevation gain
- 32 m
- Typical duration
- 10 hr
- Mountain
Hard
Massachusetts · United States
- Distance
- 20.6 km / 12.8 mi
- Elevation gain
- 47 m
- Typical duration
- 4 hr 32 min
Expert
Massachusetts · United States
- Distance
- 58.0 km / 36.1 mi
- Elevation gain
- 1,841 m
- Typical duration
- 16 hr
- Mountain
Expert
Massachusetts · United States
- Distance
- 97.5 km / 60.6 mi
- Elevation gain
- 536 m
- Typical duration
- 23 hr
- Mountain
- Long-distance path
Hard
Massachusetts · United States
- Distance
- 13.0 km / 8.1 mi
- Elevation gain
- 705 m
- Typical duration
- 3 hr 46 min
Expert
Massachusetts · United States
- Distance
- 37.8 km / 23.5 mi
- Elevation gain
- 557 m
- Typical duration
- 9 hr 24 min
- Mountain
Expert
Massachusetts · United States
- Distance
- 52.9 km / 32.9 mi
- Elevation gain
- 362 m
- Typical duration
- 12 hr
- Mountain
Hard
Massachusetts · United States
- Distance
- 27.2 km / 16.9 mi
- Elevation gain
- 289 m
- Typical duration
- 6 hr 28 min
Hard
Massachusetts · United States
- Distance
- 18.9 km / 11.7 mi
- Elevation gain
- 167 m
- Typical duration
- 4 hr 18 min
Hard
Massachusetts · United States
- Distance
- 23.3 km / 14.5 mi
- Elevation gain
- 213 m
- Typical duration
- 5 hr 26 min
Hard
Massachusetts · United States
- Distance
- 22.9 km / 14.2 mi
- Elevation gain
- 89 m
- Typical duration
- 5 hr 8 min
Hard
Massachusetts · United States
- Distance
- 26.0 km / 16.2 mi
- Elevation gain
- 91 m
- Typical duration
- 5 hr 53 min
Hard
Massachusetts · United States
- Distance
- 28.1 km / 17.5 mi
- Elevation gain
- 140 m
- Typical duration
- 6 hr 28 min
Hard
Massachusetts · United States
- Distance
- 27.5 km / 17.1 mi
- Elevation gain
- 515 m
- Typical duration
- 6 hr 53 min
Hard
Massachusetts · United States
- Distance
- 20.4 km / 12.7 mi
- Elevation gain
- 134 m
- Typical duration
- 4 hr 37 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 |
|---|---|---|---|---|---|
| Appalachian TrailMassachusetts | 140 km | 3,455 m | 38 hr | Expert | April to October |
| Midstate TrailMassachusetts | 150 km | 1,611 m | 37 hr | Expert | April to October |
| South Taconic TrailMassachusetts | 30.0 km | 1,346 m | 8 hr 43 min | Expert | April to October |
| Wapack TrailMassachusetts | 33.3 km | 1,278 m | 9 hr 24 min | Expert | April to October |
| Jones Nose to SummitMassachusetts | 13.2 km | 706 m | 3 hr 48 min | Hard | April to October |
| Robert Frost TrailMassachusetts | 68.4 km | 1,504 m | 18 hr | Expert | April to October |
| Bay Circuit TrailMassachusetts | 381 km | 774 m | 91 hr | Expert | April to October |
| Mahican-Mohawk Trail (M-M)Massachusetts | 31.8 km | 1,253 m | 9 hr 1 min | Expert | April to October |
| Warner TrailMassachusetts | 50.9 km | 508 m | 12 hr | Expert | April to October |
| Tully TrailMassachusetts | 35.7 km | 684 m | 9 hr 6 min | Expert | April to October |
Appalachian Trail, Midstate Trail, South Taconic Trail 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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