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Hemlock Hills



2.3 mile 3.7 kilometer loop
91% Runnable


Ascent: 294' 89 m
Descent: -294' -89 m
High: 771' 235 m
Low: 596' 182 m


Avg Grade: 5% (3°)
Max Grade: 17% (10°)


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Trail shared by Tom Robson

Flora and fauna abound on this short run, giving it a backcountry feel.

Tom Robson

Features Fall Colors · Lake · River/Creek · Views · Wildlife


Mountain Laurel (the CT state flower), swamp, and granite litter this quick route with awesome sites, sounds, and places to play. Try this run in Spring when everything is in bloom.

Keep an eye out for poison ivy and ticks.


From the Lake Windwing parking area, head straight east, past the iron gate on Red Trail. Take this doubletrack section to Windwing Connector, a short but very steep singletrack heading north into the woods. At the top of this trail look for obvious Orange blazes, and head straight (left, but not onto Green Trail - Red Maple Swamp) on Orange Access Trail - West. This wide, easy lane will lead you to Yellow Trail - Pine Mountain, take this on your right.

Climb an easy grade to the top of the Hemlock Hills ridge on this rocky and wooded singletrack. From here the trail continues east and passes some amazing rock formations and swamps as it runs in conjunction with Blue Trail. Eventually, Yellow stays east as Blue Trail veers away to the north. The trail then descends the ridge and intersects with Blue Connector. Take this on your right.

After some easy contouring, Blue Connector will eventually spit you out at a fork with Red Trail - turn right. Follow the Red blazes as the trail bends right, contours over large granite outcrops, and then heads west. From here the trail undulates through more rocks, occasionally showing awesome views of hills to the south as it trends generally uphill. Finally, after some tight switchbacks, Red Trail heads south and plummets towards the creek connecting Rainbow Lake to Lake Windwing.

Once the trail turns to the right (west), it becomes doubletrack and winds lazily to the shores of Lake Windwing. Continue past Orange Access Trail - West and Connector until you reach the parking area on North Shore Drive.

Flora & Fauna

  • Wild Turkey
  • Coyotes
  • Foxes
  • Deer
  • Beaver

  • Hemlock
  • Foam Flower
  • Cattail Reed
  • Bull Lily
  • Trillium
  • Bloodroot
  • Jackin-the-pulpit
  • Mountain Laurel

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Land Manager: Ridgefield Open Space

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Trail Ratings

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  3.8 from 4 votes
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in Connecticut


327 Views Last Month
4,376 Since Dec 26, 2014



A runner on Blue Trail
Dec 26, 2014 near Ridgefield, CT
Hemlock Hills-Pine Mountain map
Sep 23, 2019 near Ridgefield, CT
Beautiful creek bisecting Blue Connector trail.
Dec 27, 2014 near Ridgefield, CT
Glassy view of Lake Windwing.
Dec 26, 2014 near Ridgefield, CT
This snake was sunning itself on a plank of wood at the end of the lake on the other side of the path, down in the ravine.
Jun 13, 2016 near Ridgefield, CT
Great example of East Coast rocks on the Red Trail.
Dec 27, 2014 near Ridgefield, CT


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