Best trails near Brewster

9 trails · 9 ranked · updated 2026-06-28 · off-season

Explore the best trails near Brewster, 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 9 of 9 trails · best 15 shown on the map
N⛰
Nook Road Trail
#1 Nook Road Trail
2.5 mi away
Why 57: intrinsic quality
57Solid
O⛰
Ober Trail
#2 Ober Trail
2.2 mi away
Why 56: intrinsic quality
56Solid
S⛰
Silas Road
#3 Silas Road
2.7 mi away
Why 53: intrinsic quality
53Solid
C⛰
Cliff Pond Trail
#4 Cliff Pond Trail
2.4 mi away
Why 52: intrinsic quality
52Solid
E⛰
Eddy Bay Trail
#5 Eddy Bay Trail
1.7 mi away
Why 51: intrinsic quality
51Solid
J⛰
John Wing Trail
#6 John Wing Trail
2.6 mi away
Why 51: intrinsic quality
51Solid
L⛰
Little Cliff Pond Trail
#7 Little Cliff Pond Trail
2.8 mi away
Why 51: intrinsic quality
51Solid
W⛰
Woods Loop
#8 Woods Loop
1.8 mi away
Why 50: intrinsic quality
50Solid
R⛰
Ruth Pond Trail
#9 Ruth Pond Trail
2.1 mi away
Why 46: intrinsic quality
46Rated

Trails near Brewster

The Brewster area has 9 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 Brewster

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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