Best trails near Oakland

8 trails · 8 ranked · updated 2026-06-28 · off-season

Explore the best trails near Oakland, Maine — 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 8 of 8 trails · best 15 shown on the map
S⛰
Sanders Hill Trail
#1 Sanders Hill Trail
2.6 mi away
Why 52: intrinsic quality
52Solid
T⛰
The Mountain Trail
#2 The Mountain Trail
2.7 mi away
Why 52: intrinsic quality
52Solid
M⛰
Mount Phillip Trail
#3 Mount Phillip Trail
0.5 mi away
Why 51: intrinsic quality
51Solid
F⛰
French's Mountain Trail
#4 French's Mountain Trail
1.9 mi away
Why 51: intrinsic quality
51Solid
O⛰
Outer Loop
#5 Outer Loop
2.7 mi away
Why 51: intrinsic quality
51Solid
M⛰
Main Trail
#6 Main Trail
2.9 mi away
Why 51: intrinsic quality
51Solid
G⛰
Great Pond Loop
#7 Great Pond Loop
2.7 mi away
Why 50: intrinsic quality
50Solid
L⛰
Long Pond Loop
#8 Long Pond Loop
2.7 mi away
Why 50: intrinsic quality
50Solid

Trails near Oakland

The Oakland area has 8 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.

More trails in Maine

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