Best trails near Milford

39 trails · 39 ranked · updated 2026-06-28 · off-season

Explore the best trails near Milford, Massachusetts — every spot ranked by our conditions-aware Snoflo score: live conditions first, then visitor reviews and logged trips. Click a pin on the map for the score and what's driving it.

Showing the top 15 of 39 trails · best 15 shown on the map
W
White Trail
#1 White Trail
1.6 mi away
Why 60: intrinsic quality
60Solid
U
Upper Charles Trail
#2 Upper Charles Trail
0.6 mi away
Why 59: intrinsic quality
59Solid
T
The Parklands Blue Trail
#3 The Parklands Blue Trail
2.0 mi away
Why 57: intrinsic quality
57Solid
N
Nemba Loop
#4 Nemba Loop
1.2 mi away
Why 56: intrinsic quality
56Solid
U
Upper Charles Trail Phase 3
#5 Upper Charles Trail Phase 3
1.2 mi away
Why 56: intrinsic quality
56Solid
M
Middle Sister
#6 Middle Sister
1.5 mi away
Why 56: intrinsic quality
56Solid
T
The Main Trail
#7 The Main Trail
1.5 mi away
Why 56: intrinsic quality
56Solid
S
Swamp Bypass
#8 Swamp Bypass
1.8 mi away
Why 56: intrinsic quality
56Solid
H
Holliston Highway
#9 Holliston Highway
1.9 mi away
Why 56: intrinsic quality
56Solid
M
Milford Byway
#10 Milford Byway
1.9 mi away
Why 56: intrinsic quality
56Solid
O
Orange Trail - College Rock Park
#11 Orange Trail - College Rock Park
2.6 mi away
Why 56: intrinsic quality
56Solid
U
Upper Charles Trail Phase Connector
#12 Upper Charles Trail Phase Connector
1.0 mi away
Why 55: intrinsic quality
55Solid
C
C4
#13 C4
1.2 mi away
Why 55: intrinsic quality
55Solid
L
Linkin' Logs
#14 Linkin' Logs
1.3 mi away
Why 55: intrinsic quality
55Solid
L
Lower Three Ledges
#15 Lower Three Ledges
1.4 mi away
Why 55: intrinsic quality
55Solid

Trails near Milford

The Milford area has 39 trails on Snoflo, ranked by live conditions, visitor reviews, and logged trips — so the best, closest options rise to the top.

How we rank the best trails near Milford

How are these trails ranked?

Each gets a daily Snoflo score blending live conditions, visitor review ratings, and logged trips. The order reflects what's best right now and re-ranks every day.

How often does it update?

Daily, as new conditions, reviews, and trips arrive — so "best right now" means right now.

What do the numbers on the map mean?

Each pin shows that spot's current Snoflo score; tap it for the breakdown and a link to the full report.

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