Best trails near Chester

7 trails · 7 ranked · updated 2026-06-28 · off-season

Explore the best trails near Chester, New York — 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 7 of 7 trails · best 15 shown on the map
O⛰
Orange Heritage Trail
#1 Orange Heritage Trail
2.7 mi away
Why 61: intrinsic quality
61Solid
O⛰
Orange Heritage Trailway
#2 Orange Heritage Trailway
1.7 mi away
Why 59: intrinsic quality
59Solid
O⛰
Orange Heritage Trail
#3 Orange Heritage Trail
2.7 mi away
Why 56: intrinsic quality
56Solid
B⛰
Bridge #2
#4 Bridge #2
2.2 mi away
Why 55: intrinsic quality
55Solid
B⛰
Bridge #3
#5 Bridge #3
2.5 mi away
Why 55: intrinsic quality
55Solid
B⛰
Bridge #4
#6 Bridge #4
2.5 mi away
Why 55: intrinsic quality
55Solid
L⛰
Lazy Hill Road
#7 Lazy Hill Road
1.3 mi away
Why 52: intrinsic quality
52Solid

Trails near Chester

The Chester area has 7 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 Chester

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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