Best trails near Lenox

26 trails · 26 ranked · updated 2026-06-28 · off-season

Explore the best trails near Lenox, 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 26 trails · best 15 shown on the map
Y
Yokun Ridge Trail
#1 Yokun Ridge Trail
2.8 mi away
Why 57: intrinsic quality
57Solid
W
Woolsey
#2 Woolsey
1.0 mi away
Why 56: intrinsic quality
56Solid
C
Coakley/Main
#3 Coakley/Main
1.2 mi away
Why 56: intrinsic quality
56Solid
A
Aspinwall
#4 Aspinwall
1.2 mi away
Why 56: intrinsic quality
56Solid
L
Log Hop
#5 Log Hop
1.4 mi away
Why 56: intrinsic quality
56Solid
O
October Mountain Loop Trail
#6 October Mountain Loop Trail
2.3 mi away
Why 55: intrinsic quality
55Solid
B
Burbank Trail
#7 Burbank Trail
3.0 mi away
Why 53: intrinsic quality
53Solid
B
Boulder Trail
#8 Boulder Trail
2.9 mi away
Why 52: intrinsic quality
52Solid
B
Boulder Trail (orange)
#9 Boulder Trail (orange)
2.9 mi away
Why 52: intrinsic quality
52Solid
R
Roaring Brook Road
#10 Roaring Brook Road
1.6 mi away
Why 51: intrinsic quality
51Solid
W
Woodland Road
#11 Woodland Road
1.8 mi away
Why 51: intrinsic quality
51Solid
S
Schemerhorn Trail
#12 Schemerhorn Trail
2.0 mi away
Why 51: intrinsic quality
51Solid
S
Switchback Trail
#13 Switchback Trail
2.0 mi away
Why 51: intrinsic quality
51Solid
G
Gorge Trail (North Side)
#14 Gorge Trail (North Side)
2.1 mi away
Why 51: intrinsic quality
51Solid
G
Gorge Trail (South Side)
#15 Gorge Trail (South Side)
2.1 mi away
Why 51: intrinsic quality
51Solid

Trails near Lenox

The Lenox area has 26 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 Lenox

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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