Best trails near Oakland

59 trails · 59 ranked · updated 2026-06-28 · off-season

Explore the best trails near Oakland, New Jersey — 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 59 trails · best 15 shown on the map
C⛰
Cannonball Trail
#1 Cannonball Trail
2.2 mi away
Why 60: intrinsic quality
60Solid
W⛰
Wanaque Ridge Trail
#2 Wanaque Ridge Trail
1.6 mi away
Why 58: intrinsic quality
58Solid
C⛰
Castle Loop Trail
#3 Castle Loop Trail
1.2 mi away
Why 57: intrinsic quality
57Solid
R⛰
Rye Cliff Road
#4 Rye Cliff Road
1.0 mi away
Why 56: intrinsic quality
56Solid
S⛰
South Shore Drive/Ramapo Lake Loop Trail
#5 South Shore Drive/Ramapo Lake Loop Trail
1.1 mi away
Why 56: intrinsic quality
56Solid
R⛰
Ramapo Lake Loop
#6 Ramapo Lake Loop
1.2 mi away
Why 56: intrinsic quality
56Solid
F⛰
Foxcroft Road
#7 Foxcroft Road
1.4 mi away
Why 56: intrinsic quality
56Solid
R⛰
Ramapo Lake Loop/Cannonball Trail
#8 Ramapo Lake Loop/Cannonball Trail
1.4 mi away
Why 56: intrinsic quality
56Solid
P⛰
Pool Hollow Trail
#9 Pool Hollow Trail
1.5 mi away
Why 56: intrinsic quality
56Solid
W⛰
Wanaque Ridge Spur Trail
#10 Wanaque Ridge Spur Trail
1.7 mi away
Why 56: intrinsic quality
56Solid
S⛰
South Ridge Trail
#11 South Ridge Trail
1.8 mi away
Why 56: intrinsic quality
56Solid
P⛰
Pete's Path
#12 Pete's Path
2.0 mi away
Why 56: intrinsic quality
56Solid
C⛰
Cresent
#13 Cresent
2.0 mi away
Why 56: intrinsic quality
56Solid
H⛰
Highlands Rail Trail
#14 Highlands Rail Trail
2.7 mi away
Why 56: intrinsic quality
56Solid
R⛰
Ramapo Lake Spur/Castle Loop Trail
#15 Ramapo Lake Spur/Castle Loop Trail
0.9 mi away
Why 55: intrinsic quality
55Solid

Trails near Oakland

The Oakland area has 59 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 Oakland

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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