Best trails near Milton

34 trails · 34 ranked · updated 2026-06-28 · off-season

Explore the best trails near Milton, 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 34 trails · best 15 shown on the map
N
Neponset River Greenway
#1 Neponset River Greenway
2.1 mi away
Why 59: intrinsic quality
59Solid
S
Skyline Trail
#2 Skyline Trail
1.3 mi away
Why 58: intrinsic quality
58Solid
W
Walking City Trail Section 1
#3 Walking City Trail Section 1
2.7 mi away
Why 57: intrinsic quality
57Solid
B
Burma Road Trail
#4 Burma Road Trail
2.9 mi away
Why 57: intrinsic quality
57Solid
N
Neponset River Greenway
#5 Neponset River Greenway
2.1 mi away
Why 56: intrinsic quality
56Solid
S
Skyline Trail South
#6 Skyline Trail South
2.2 mi away
Why 56: intrinsic quality
56Solid
C
Coon Hollow Path
#7 Coon Hollow Path
2.4 mi away
Why 56: intrinsic quality
56Solid
B
Blue Hill River Road
#8 Blue Hill River Road
2.5 mi away
Why 56: intrinsic quality
56Solid
P
Ponkapoag Trail
#9 Ponkapoag Trail
3.0 mi away
Why 56: intrinsic quality
56Solid
B
Breakneck Ledge Path
#10 Breakneck Ledge Path
1.7 mi away
Why 55: intrinsic quality
55Solid
B
Breakneck Ledge Path
#11 Breakneck Ledge Path
1.9 mi away
Why 55: intrinsic quality
55Solid
D
Dark Hollow Path
#12 Dark Hollow Path
1.9 mi away
Why 55: intrinsic quality
55Solid
H
Harvest River Bridge
#13 Harvest River Bridge
1.9 mi away
Why 55: intrinsic quality
55Solid
N
Neponset River Greenway
#14 Neponset River Greenway
1.9 mi away
Why 55: intrinsic quality
55Solid
H
Headquarters Path
#15 Headquarters Path
2.1 mi away
Why 55: intrinsic quality
55Solid

Trails near Milton

The Milton area has 34 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 Milton

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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