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Moderate Hiking Trails near Boston

The directory currently contains 43 quality-checked routes matching this guide near Boston. Their average mapped distance is 7.5 km and average recorded ascent is 94 m (308 ft); the longest route in the set is 16.6 km.

This subset represents 24% of the 177 quality-checked routes near Boston. Its average distance is 7.5 km, compared with 8.7 km across the full local set. Average recorded ascent is 94 m (308 ft), versus 63 m (207 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 8 (19%) 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

1.2 km

Blue Trail

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

Lowest recorded ascent in this sample

57 m

Blue Trail

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

Town Forest Loop Trail

Massachusetts · United States

Distance
9.5 km
/ 5.9 mi
Elevation gain
68 m
Typical duration
2 hr 5 min
  • Forest
  • Waymarked route
Moderate

ALD ACROSS Lexington Route D

Massachusetts · United States

Distance
5.7 km
/ 3.5 mi
Elevation gain
63 m
Typical duration
1 hr 17 min
  • Waymarked route
Moderate

Blue Trail

Massachusetts · United States

Distance
1.2 km
/ 0.8 mi
Elevation gain
57 m
Typical duration
21 min
  • Waymarked route
Middlesex Fells, Medford, United States
Moderate

Cross Fells Trail

Massachusetts · United States

Distance
7.5 km
/ 4.6 mi
Elevation gain
123 m
Typical duration
1 hr 44 min
  • Waymarked route
Moderate

Crystal Spring Trail

Massachusetts · United States

Distance
2.3 km
/ 1.4 mi
Elevation gain
68 m
Typical duration
34 min
  • Waymarked route
Moderate

Red Trail

Massachusetts · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
18 m
Typical duration
13 min
  • Waymarked route
Moderate

Reservoir Trail

Massachusetts · United States

Distance
9.5 km
/ 5.9 mi
Elevation gain
135 m
Typical duration
2 hr 11 min
  • Waymarked route
Moderate

Rock Circuit Trail

Massachusetts · United States

Distance
6.5 km
/ 4.1 mi
Elevation gain
147 m
Typical duration
1 hr 35 min
  • Waymarked route
Moderate

Skyline Trail

Massachusetts · United States

Distance
11.8 km
/ 7.3 mi
Elevation gain
230 m
Typical duration
2 hr 48 min
  • Waymarked route
Vestigial railroad tracks along side the w:Minuteman Bikeway in Lexington, Massachusetts.
Moderate

ACROSS Lexington Route A

Massachusetts · United States

Distance
8.4 km
/ 5.3 mi
Elevation gain
23 m
Typical duration
1 hr 48 min
  • Waymarked route
Buckman Tavern in Lexington , Massachusetts ( United States ).
Moderate

ACROSS Lexington Route E

Massachusetts · United States

Distance
7.5 km
/ 4.7 mi
Elevation gain
49 m
Typical duration
1 hr 39 min
  • Waymarked route
Sunset, First Parish Church, Lexington Massachusetts.
Moderate

ACROSS Lexington Route F

Massachusetts · United States

Distance
10.4 km
/ 6.4 mi
Elevation gain
111 m
Typical duration
2 hr 20 min
  • Waymarked route
Acton Minutemen and citizens marching from Acton to Concord on Patriots Day 2012
Moderate

BCT 6 Acton/Concord

Massachusetts · United States

Distance
14.8 km
/ 9.2 mi
Elevation gain
81 m
Typical duration
3 hr 12 min
Moderate

Ridge Trail

Massachusetts · United States

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

BoundaryTrail

Massachusetts · United States

Distance
5.4 km
/ 3.3 mi
Elevation gain
125 m
Typical duration
1 hr 18 min
Moderate

Cat Rock Loop

Massachusetts · United States

Distance
4.1 km
/ 2.6 mi
Elevation gain
80 m
Typical duration
59 min
Moderate

Two Brothers Trail

Massachusetts · United States

Distance
2.1 km
/ 1.3 mi
Elevation gain
54 m
Typical duration
31 min
Moderate

Western Greenway

Massachusetts · United States

Distance
11.9 km
/ 7.4 mi
Elevation gain
162 m
Typical duration
2 hr 44 min
Moderate

Battle Road Trail

Massachusetts · United States

Distance
7.6 km
/ 4.7 mi
Elevation gain
53 m
Typical duration
1 hr 40 min
Moderate

Shepley Steeplechase Trail

Massachusetts · United States

Distance
3.7 km
/ 2.3 mi
Elevation gain
70 m
Typical duration
53 min
  • River
Moderate

Mount Misery Round Trip

Massachusetts · United States

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

Bancroft Castle

Massachusetts · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
46 m
Typical duration
16 min
  • Castle and ruins
Moderate

Charm Bracelet Trail

Massachusetts · United States

Distance
11.1 km
/ 6.9 mi
Elevation gain
142 m
Typical duration
2 hr 32 min
A trail on the abandoned right-of-way of the never-used Lancaster Railroad in the Danforth Creek Property in Hudson in May 2017
Moderate

Danforth Loop

Massachusetts · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
61 m
Typical duration
27 min
Moderate

Freedom Trail

Massachusetts · United States

Distance
8.1 km
/ 5.1 mi
Elevation gain
85 m
Typical duration
1 hr 49 min
Moderate

East Groton Tour

Massachusetts · United States

Distance
12.3 km
/ 7.7 mi
Elevation gain
127 m
Typical duration
2 hr 46 min
Moderate

Jeff Smith Trail

Massachusetts · United States

Distance
8.3 km
/ 5.2 mi
Elevation gain
76 m
Typical duration
1 hr 51 min
View of Punkatasset Hill from Great Meadows National Wildlife Refuge
Moderate

Punkatasset Estabrook Loop

Massachusetts · United States

Distance
5.3 km
/ 3.3 mi
Elevation gain
98 m
Typical duration
1 hr 15 min
Moderate

White Trail

Massachusetts · United States

Distance
10.6 km
/ 6.6 mi
Elevation gain
139 m
Typical duration
2 hr 25 min
Moderate

Drumlin Hop

Massachusetts · United States

Distance
5.2 km
/ 3.2 mi
Elevation gain
220 m
Typical duration
1 hr 24 min
Moderate

Indian Hill

Massachusetts · United States

Distance
5.7 km
/ 3.5 mi
Elevation gain
79 m
Typical duration
1 hr 18 min
Moderate

Burns Hill Loop Trail

Massachusetts · United States

Distance
1.8 km
/ 1.1 mi
Elevation gain
59 m
Typical duration
28 min
Moderate

Andover Community Paths

Massachusetts · United States

Distance
4.7 km
/ 2.9 mi
Elevation gain
142 m
Typical duration
1 hr 11 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
BCT 5a & 6 Billerica/Bedford/ConcordMassachusetts16.6 km74 m3 hr 37 minModerateApril to October
Town Forest Loop TrailMassachusetts9.5 km68 m2 hr 5 minModerateApril to October
ALD ACROSS Lexington Route DMassachusetts5.7 km63 m1 hr 17 minModerateApril to October
Blue TrailMassachusetts1.2 km57 m21 minModerateApril to October
Cross Fells TrailMassachusetts7.5 km123 m1 hr 44 minModerateApril to October
Crystal Spring TrailMassachusetts2.3 km68 m34 minModerateApril to October
Red TrailMassachusetts0.9 km18 m13 minModerateApril to October
Reservoir TrailMassachusetts9.5 km135 m2 hr 11 minModerateApril to October
Rock Circuit TrailMassachusetts6.5 km147 m1 hr 35 minModerateApril to October
Skyline TrailMassachusetts11.8 km230 m2 hr 48 minModerateApril to October

BCT 5a & 6 Billerica/Bedford/Concord, Town Forest Loop Trail, Crystal Spring 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

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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.

Read article →

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