Westwoods Trail Run

Westwoods Trailhead Sign
One of the nice things about living in New Haven, CT is that it's easy to get outside. Here is a trail run I like to do on weekends in the Westwoods Trails, 20 minutes away in Guilford. This run is great because it's quiet, well-marked, and not too difficult in terms of hills. Plus, if you like mountain biking, fat-tire play is allowed here too. This run is roughly 7.5 miles.

Westwoods Trailhead

Westwoods Map
I like to start at Entrance #1 on Dunk Rock Road. This is the closest park entrance to the highway and in the fall Bishop's Orchards does raspberry picking right across the street (yum). From here, follow the Green Rectangle trail away from the parking lot. About 0.3 miles up the trail you'll come across this tree (below) that leans over the trail; turn right here and follow the Green Circle trail.
Green Circle Turnoff
The Green Circle trail takes you from a small creek valley up to a T intersection with the White Circle trail. Follow this out a dirt road to Entrance #2 at Peddlers Road. Turn around and follow the White Square trail off to your right on the far side of the dirt lot. The White Square will takes you back to the White Circle trail shortly.

Wooden Planks
You're going to stay on the White Circle for pretty much the entire length of the park. Soon after leaving the White Square, you'll drop down into a marshy low-lying area with some fun planks (left) to run over. After this, watch out at a couple of the trail intersections because they can be a little confusing, especially the White-Green Intersection and the White-Blue Intersection. At the latter, don't follow the White Rectangle or any of the Yellow trails - just stay on what seems like the White Circle trail and you'll punch through some trees, cross the Blue Rectangle and find the White Circle blazes again. I've gone in circles more than once at this spot.

Pinch in the Rock

There's a cool feature about halfway down the length of the trail, where the trail runs through a slot in the rock (right). I must seem like a madman when I run through here, because I'm always yelling and clapping my hands as I go through, because I don't want to surprise any animals that may be sleeping in there - it's a narrow path, and raccoon claws are not my friends. After this, you'll pass Lost Lake Overlook (below), where you'll often come across people enjoying the view.
Lost Lake
After Lost Lake, it's not too far to the far end of the trail at Entrance #3 on Sam Hill Road. I usually turn around here and follow the White Circle back past the railroad tracks to the White-Orange Intersection; here you bear right and follow the Orange Circle trail most of the way back to the top of the park. Midway through this section is a confusing spot where the obvious trail goes straight but you should hang a sharp left and scramble down some big rocks. If you continue straight you will come across the Orange Circle trail eventually, but it's easy to get turned around here.

To complete the run, cross the Orange-Blue Intersection and turn right at the Orange-Green Intersection. Follow the Green Rectangle trail out of the park to your original trailhead. If it's in season, feel free to stop for some raspberry picking out your way out. Have fun.