Best trails near Windsor

10 trails · 10 ranked · updated 2026-06-28 · off-season

Explore the best trails near Windsor, 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 10 of 10 trails · best 15 shown on the map
D
Day Hill Multi-Use Trail
#1 Day Hill Multi-Use Trail
1.7 mi away
Why 58: intrinsic quality
58Solid
G
Goodwin Drive Sidepath
#2 Goodwin Drive Sidepath
1.9 mi away
Why 56: intrinsic quality
56Solid
M
Michael F. Gragnolati Conservation Trail
#3 Michael F. Gragnolati Conservation Trail
3.0 mi away
Why 56: intrinsic quality
56Solid
W
Windsor River Trail
#4 Windsor River Trail
2.2 mi away
Why 51: intrinsic quality
51Solid
B
Brookside Trail
#5 Brookside Trail
2.4 mi away
Why 51: intrinsic quality
51Solid
Y
Yellow Trail
#6 Yellow Trail
2.6 mi away
Why 51: intrinsic quality
51Solid
B
Blue Trail
#7 Blue Trail
2.6 mi away
Why 50: intrinsic quality
50Solid
W
White Trail
#8 White Trail
2.6 mi away
Why 50: intrinsic quality
50Solid
R
Red Trail
#9 Red Trail
2.7 mi away
Why 50: intrinsic quality
50Solid
P
Pink Trail
#10 Pink Trail
2.8 mi away
Why 50: intrinsic quality
50Solid

Trails near Windsor

The Windsor area has 10 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 Windsor

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 Connecticut