Best trails near Woodbridge

37 trails · 37 ranked · updated 2026-06-28 · off-season

Explore the best trails near Woodbridge, Connecticut — 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 37 trails · best 15 shown on the map
N
Naugatuck Trail (Woodbridge)
#1 Naugatuck Trail (Woodbridge)
0.2 mi away
Why 61: intrinsic quality
61Solid
B
Baldwin Drive
#2 Baldwin Drive
2.5 mi away
Why 60: intrinsic quality
60Solid
M
Meadow Trail
#3 Meadow Trail
0.7 mi away
Why 56: intrinsic quality
56Solid
P
Power Cut Road
#4 Power Cut Road
1.3 mi away
Why 56: intrinsic quality
56Solid
S
Sperry Road
#5 Sperry Road
1.7 mi away
Why 56: intrinsic quality
56Solid
R
Regicides Trail
#6 Regicides Trail
2.4 mi away
Why 56: intrinsic quality
56Solid
R
Regicide Drive
#7 Regicide Drive
2.6 mi away
Why 56: intrinsic quality
56Solid
O
Old Oak Nature Trail Loop
#8 Old Oak Nature Trail Loop
2.8 mi away
Why 56: intrinsic quality
56Solid
E
East Boundary Trail
#9 East Boundary Trail
0.7 mi away
Why 55: intrinsic quality
55Solid
N
North Boundary Trail
#10 North Boundary Trail
0.8 mi away
Why 55: intrinsic quality
55Solid
W
West Boundary Trail
#11 West Boundary Trail
0.8 mi away
Why 55: intrinsic quality
55Solid
S
Sperry Road
#12 Sperry Road
1.3 mi away
Why 55: intrinsic quality
55Solid
P
Power Cut Road
#13 Power Cut Road
1.5 mi away
Why 55: intrinsic quality
55Solid
O
Old Derby Trail
#14 Old Derby Trail
1.8 mi away
Why 55: intrinsic quality
55Solid
R
Regicide Drive
#15 Regicide Drive
2.6 mi away
Why 55: intrinsic quality
55Solid

Trails near Woodbridge

The Woodbridge area has 37 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 Woodbridge

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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