Best trails near Vineyard Haven

18 trails · 18 ranked · updated 2026-06-28 · off-season

Explore the best trails near Vineyard Haven, 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 18 trails · best 15 shown on the map
P
Phillips Reserve Red Blue Trail
#1 Phillips Reserve Red Blue Trail
1.0 mi away
Why 51: intrinsic quality
51Solid
R
Ripley's Field Path
#2 Ripley's Field Path
1.3 mi away
Why 51: intrinsic quality
51Solid
S
Sailors Burying Ground Road
#3 Sailors Burying Ground Road
1.3 mi away
Why 51: intrinsic quality
51Solid
T
Tisbury Meadow
#4 Tisbury Meadow
1.4 mi away
Why 51: intrinsic quality
51Solid
O
Old Holmes Hole Road
#5 Old Holmes Hole Road
1.7 mi away
Why 51: intrinsic quality
51Solid
W
Woods Loop
#6 Woods Loop
1.7 mi away
Why 51: intrinsic quality
51Solid
S
Stoney Hill Path
#7 Stoney Hill Path
2.5 mi away
Why 51: intrinsic quality
51Solid
W
WCW Blue Trail
#8 WCW Blue Trail
1.1 mi away
Why 50: intrinsic quality
50Solid
W
WCW Yellow Trail
#9 WCW Yellow Trail
1.1 mi away
Why 50: intrinsic quality
50Solid
R
Road to Wapatequa
#10 Road to Wapatequa
1.5 mi away
Why 50: intrinsic quality
50Solid
E
Elderberry
#11 Elderberry
2.4 mi away
Why 50: intrinsic quality
50Solid
H
Holly
#12 Holly
2.4 mi away
Why 50: intrinsic quality
50Solid
L
Lilac
#13 Lilac
2.4 mi away
Why 50: intrinsic quality
50Solid
P
Pansy
#14 Pansy
2.4 mi away
Why 50: intrinsic quality
50Solid
T
Thyme
#15 Thyme
2.4 mi away
Why 50: intrinsic quality
50Solid

Trails near Vineyard Haven

The Vineyard Haven area has 18 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 Vineyard Haven

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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