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Hiking Trails Under 5 km in Massachusetts

The directory currently contains 199 quality-checked routes matching this guide in Massachusetts. Their average mapped distance is 2.2 km and average recorded ascent is 43 m (141 ft); the longest route in the set is 5.0 km.

This subset represents 66% of the 300 quality-checked routes in Massachusetts. Its average distance is 2.2 km, compared with 9.0 km across the full local set. Average recorded ascent is 43 m (141 ft), versus 124 m (407 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, 150 routes (75%) are rated easy, 0 (0%) are rated hard or expert, and 48 (24%) 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

0.6 km

Virginia Wood Trail

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

Lowest recorded ascent in this sample

0 m

Great Meadows Bird Observer Trail

6 of 6 have ascent data. Missing measurements are excluded.

Return logistics

2 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

Virginia Wood Trail

Massachusetts · United States

Distance
0.6 km
/ 0.4 mi
Elevation gain
18 m
Typical duration
9 min
  • Forest
  • Waymarked route
Easy

Woodland Path Loop

Massachusetts · United States

Distance
1.0 km
/ 0.6 mi
Elevation gain
16 m
Typical duration
14 min
  • Forest
  • Waymarked route
Easy

Sabine Woods Loop

Massachusetts · United States

Distance
4.3 km
/ 2.7 mi
Elevation gain
35 m
Typical duration
57 min
  • River
  • Forest
Moderate

Blue Trail

Massachusetts · United States

Distance
1.2 km
/ 0.8 mi
Elevation gain
57 m
Typical duration
21 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
Easy

Balsam Trail

Massachusetts · United States

Distance
2.2 km
/ 1.4 mi
Elevation gain
9 m
Typical duration
28 min
  • Waymarked route
Easy

Fells Path

Massachusetts · United States

Distance
0.7 km
/ 0.4 mi
Typical duration
8 min
  • Waymarked route
Easy

Historic Trail

Massachusetts · United States

Distance
1.5 km
/ 1.0 mi
Elevation gain
30 m
Typical duration
22 min
  • Waymarked route
Easy

Long Pond Nature Trail

Massachusetts · United States

Distance
2.0 km
/ 1.2 mi
Elevation gain
20 m
Typical duration
27 min
  • Waymarked route
Easy

Pond Passage Loop

Massachusetts · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
13 m
Typical duration
23 min
  • Waymarked route
Easy

Rock Circuit Connector

Massachusetts · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
35 m
Typical duration
15 min
  • Waymarked route
Easy

Thompson Pond Trail

Massachusetts · United States

Distance
1.7 km
/ 1.1 mi
Elevation gain
7 m
Typical duration
22 min
  • Waymarked route
Easy

Twin Pond Trail

Massachusetts · United States

Distance
2.4 km
/ 1.5 mi
Elevation gain
6 m
Typical duration
31 min
  • Waymarked route
Moderate

Mountain House Trail

Massachusetts · United States

Distance
1.4 km
/ 0.9 mi
Typical duration
17 min
  • Mountain
Easy

Long Lake Loop

Massachusetts · United States

Distance
3.0 km
/ 1.9 mi
Elevation gain
67 m
Typical duration
44 min
  • Lake
Easy

Yellow Loop

Massachusetts · United States

Distance
3.6 km
/ 2.3 mi
Elevation gain
80 m
Typical duration
53 min
  • Waymarked route
Easy

Lower Vine Brook Loop

Massachusetts · United States

Distance
1.1 km
/ 0.7 mi
Elevation gain
10 m
Typical duration
15 min
  • River
Easy

Codman Forest Loop

Massachusetts · United States

Distance
2.3 km
/ 1.4 mi
Elevation gain
8 m
Typical duration
29 min
  • Forest
Moderate

Ridge Trail

Massachusetts · United States

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

Billy Goat Trail

Massachusetts · United States

Distance
0.7 km
/ 0.4 mi
Elevation gain
113 m
Typical duration
18 min
  • Waymarked route
Moderate

Kathy's Trail

Massachusetts · United States

Distance
0.7 km
/ 0.5 mi
Elevation gain
84 m
Typical duration
17 min
  • Waymarked route
Easy

Main Trail (blue)

Massachusetts · United States

Distance
1.1 km
/ 0.7 mi
Typical duration
13 min
  • Waymarked route
Moderate

North Trail

Massachusetts · United States

Distance
0.8 km
/ 0.5 mi
Elevation gain
32 m
Typical duration
12 min
  • Waymarked route
Easy

Old Coach Trail

Massachusetts · United States

Distance
1.6 km
/ 1.0 mi
Elevation gain
41 m
Typical duration
24 min
  • Waymarked route
Easy

Clam River Loop

Massachusetts · United States

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

Blue Route

Massachusetts · United States

Distance
2.0 km
/ 1.2 mi
Elevation gain
9 m
Typical duration
26 min
  • Waymarked route
[The North Main Street (Route 27) bridge over the Worcester Main Line seen from the inbound platform at Natick station in December 2006
Easy

North Trail

Massachusetts · United States

Distance
1.1 km
/ 0.7 mi
Elevation gain
7 m
Typical duration
14 min
  • Waymarked route
Easy

Pegan Cove

Massachusetts · United States

Distance
0.6 km
/ 0.4 mi
Typical duration
7 min
  • Waymarked route
Easy

blue trail

Massachusetts · United States

Distance
0.5 km
/ 0.3 mi
Typical duration
6 min
  • Waymarked route
Moderate

Cat Rock Loop

Massachusetts · United States

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

Interior Loop Trail

Massachusetts · United States

Distance
1.6 km
/ 1.0 mi
Elevation gain
45 m
Typical duration
24 min
Easy

Tom Paul Trail

Massachusetts · United States

Distance
4.3 km
/ 2.7 mi
Elevation gain
29 m
Typical duration
57 min
Moderate

Two Brothers Trail

Massachusetts · United States

Distance
2.1 km
/ 1.3 mi
Elevation gain
54 m
Typical duration
31 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
Great Meadows Bird Observer TrailMassachusetts4.7 km0 m59 minEasyApril to October
Virginia Wood TrailMassachusetts0.6 km18 m9 minEasyApril to October
Woodland Path LoopMassachusetts1.0 km16 m14 minEasyApril to October
Sabine Woods LoopMassachusetts4.3 km35 m57 minEasyApril to October
Blue TrailMassachusetts1.2 km57 m21 minModerateApril to October
Crystal Spring TrailMassachusetts2.3 km68 m34 minModerateApril to October
Red TrailMassachusetts0.9 km18 m13 minModerateApril to October
Simon's Rock Interpretive TrailMassachusetts1.4 km51 m22 minModerateApril to October
ALC ACROSS Lexington Route CMassachusetts4.1 km12 m52 minEasyApril to October

Cheshire Harbor Trail, Virginia Wood Trail, Great Meadows Bird Observer 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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