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Best Mountain Hikes in Massachusetts

The directory currently contains 30 quality-checked routes matching this guide in Massachusetts. Their average mapped distance is 45.3 km and average recorded ascent is 641 m (2,103 ft); the longest route in the set is 381 km.

This subset represents 10% of the 300 quality-checked routes in Massachusetts. Its average distance is 45.3 km, compared with 9.0 km across the full local set. Average recorded ascent is 641 m (2,103 ft), versus 124 m (407 ft) for all quality-checked routes in the same area.

These routes carry the mountain tag. Their measured distance and ascent are shown separately so the label is not used as a proxy for difficulty. Within this set, 2 routes (7%) are rated easy, 17 (57%) are rated hard or expert, and 2 (7%) 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 Summit

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

Lowest recorded ascent in this sample

706 m

Jones Nose to Summit

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

Expert

Appalachian Trail

Massachusetts · United States

Distance
140 km
/ 87.2 mi
Elevation gain
3,455 m
Typical duration
38 hr
  • Mountain
  • Waymarked route
  • Long-distance path
Expert

Midstate Trail

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

South Taconic Trail

Massachusetts · United States

Distance
30.0 km
/ 18.7 mi
Elevation gain
1,346 m
Typical duration
8 hr 43 min
  • Mountain
  • Waymarked route
Wapack National Wildlife Refuge. Credit: Matt Poole/USFWS. Like us on Facebook: facebook.com/USFWSNortheast Follow us on Twitter: twitter.com/USFWSNortheast
Expert

Wapack Trail

Massachusetts · United States

Distance
33.3 km
/ 20.7 mi
Elevation gain
1,278 m
Typical duration
9 hr 24 min
  • Mountain
  • Waymarked route
Monument atop Mount Greylock at sunset
Hard

Jones Nose to Summit

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

Robert Frost Trail

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

Bay Circuit Trail

Massachusetts · United States

Distance
381 km
/ 237 mi
Elevation gain
774 m
Typical duration
91 hr
  • Mountain
  • Long-distance path
Expert

Mahican-Mohawk Trail (M-M)

Massachusetts · United States

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

Warner Trail

Massachusetts · United States

Distance
50.9 km
/ 31.6 mi
Elevation gain
508 m
Typical duration
12 hr
  • Mountain
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
Moderate

Watatic Summit

Massachusetts · United States

Distance
5.3 km
/ 3.3 mi
Elevation gain
246 m
Typical duration
1 hr 29 min
  • Mountain
  • Summit push
  • Panoramic viewpoint
Westward view from Thatcher Ledges
Expert

Tully Trail

Massachusetts · United States

Distance
35.7 km
/ 22.2 mi
Elevation gain
684 m
Typical duration
9 hr 6 min
  • Mountain
Expert

BCT Section 2

Massachusetts · United States

Distance
44.8 km
/ 27.9 mi
Elevation gain
210 m
Typical duration
10 hr
  • Mountain
Sunset on Long Pond, Plymouth, Massachusetts, USA, from a w:Pinewoods Camp canoe.
Expert

Plymouth Wishbone Trail

Massachusetts · United States

Distance
40.4 km
/ 25.1 mi
Elevation gain
309 m
Typical duration
9 hr 39 min
  • Mountain
Moderate

Mountain House Trail

Massachusetts · United States

Distance
1.4 km
/ 0.9 mi
Typical duration
17 min
  • Mountain
The Boston Design Center and the Cruiseport. Shot with Canon EOS REBEL T1i - EF-S17-85mm f/4-5.6 IS USM @ 47 ¹⁄₂₅₀ sec at f/11 - 100 - no flash
Expert

Boston HarborWalk

Massachusetts · United States

Distance
46.0 km
/ 28.6 mi
Elevation gain
32 m
Typical duration
10 hr
  • Mountain
Moderate

Wilbur’s Clearing to Summit

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
Expert

Taconic Crest Trail

Massachusetts · United States

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

The Cape Cod Way

Massachusetts · United States

Distance
97.5 km
/ 60.6 mi
Elevation gain
536 m
Typical duration
23 hr
  • Mountain
  • Long-distance path
Moderate

Ridge Trail

Massachusetts · United States

Distance
3.0 km
/ 1.9 mi
Elevation gain
68 m
Typical duration
44 min
  • Mountain
Expert

Corridor 71

Massachusetts · United States

Distance
37.8 km
/ 23.5 mi
Elevation gain
557 m
Typical duration
9 hr 24 min
  • Mountain
Expert

Mystic Link Trail

Massachusetts · United States

Distance
52.9 km
/ 32.9 mi
Elevation gain
362 m
Typical duration
12 hr
  • Mountain
Moderate

Peaked Mountain Orange Trails

Massachusetts · United States

Distance
1.6 km
/ 1.0 mi
Elevation gain
99 m
Typical duration
28 min
  • Mountain
  • Waymarked route
Easy

Peaked Mountain Pink Trails

Massachusetts · United States

Distance
1.2 km
/ 0.7 mi
Elevation gain
64 m
Typical duration
21 min
  • Mountain
  • Waymarked route
Moderate

Peaked Mountain Red Trails

Massachusetts · United States

Distance
2.4 km
/ 1.5 mi
Elevation gain
49 m
Typical duration
35 min
  • Mountain
  • Waymarked route
Moderate

Peaked Mountain White Trails

Massachusetts · United States

Distance
1.5 km
/ 0.9 mi
Elevation gain
190 m
Typical duration
36 min
  • Mountain
  • Waymarked route
Easy

Peaked Mountain Yellow Trails

Massachusetts · United States

Distance
0.6 km
/ 0.4 mi
Elevation gain
41 m
Typical duration
11 min
  • Mountain
  • Waymarked route
Moderate

October Mountain Loop Trail

Massachusetts · United States

Distance
10.5 km
/ 6.5 mi
Elevation gain
430 m
Typical duration
2 hr 50 min
  • Mountain
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

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
Midstate TrailMassachusetts150 km1,611 m37 hrExpertApril to October
South Taconic TrailMassachusetts30.0 km1,346 m8 hr 43 minExpertApril to October
Wapack TrailMassachusetts33.3 km1,278 m9 hr 24 minExpertApril to October
Jones Nose to SummitMassachusetts13.2 km706 m3 hr 48 minHardApril to October
Robert Frost TrailMassachusetts68.4 km1,504 m18 hrExpertApril to October
Bay Circuit TrailMassachusetts381 km774 m91 hrExpertApril to October
Mahican-Mohawk Trail (M-M)Massachusetts31.8 km1,253 m9 hr 1 minExpertApril to October
Warner TrailMassachusetts50.9 km508 m12 hrExpertApril to October
Cheshire Harbor TrailMassachusetts2.0 km159 m39 minModerateApril 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 →

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