The Westwoods is run by the Guilford Land trust and has a total of 39 miles of networked trails in 1200 acres near Guilford in CT. It contains the biggest variety of features I’ve seen in CT including salt marshes, lakes, waterfalls, rock formations ( and various features to squeeze or walk through) an Old Leatherman Cave, various other caves and continues to be one of my favourite spots in all of Connecticut for woodland.

Full Guide

I’ve now hiked or run almost all of the major trail systems in Connecticut and I still rate Westwoods as my absolute favorite place in CT to visit because of the variety. Every time I visit I find a new feature or enjoy new parts of it. The large network of criss crossed colored trails means you can pick your distance and route with an almost infinite combination and some of the features here are the most fun and cool I’ve seen in the state.

The Old Leatherman Cave

On the green blazed trail near the west section of the woods is an Old Leatherman Cave that he used to use monthly on his 350 mile loop he used to walk in the 1880s. I used part of Westwoods to create the Old Leatherman Loop where I recreated his iconic route.

Lost Lake Overlook

The White Trails start near the southern tip of the Westwoods and head north taking in the ‘Lost Lake’. This rocky ledge gives you views of the tidal brackish lake that leads out to sea.

The Little Squeeze

The Little Squeeze is on the Yellow Dot trail and features and very very small gap that the trail goes through.

If you don’t fancy tight spaces almost all of the features in Westwoods have an alternate path going round these kooky bits.

The Crawl

The Yellow Dot trail also has the rock feature called ‘The Crawl’ which involves dropping into to a crack in the rock and moving along through it.

Joes Cave

The orange dot trail features Joes Cave which is an overhang in a stunning rocky ledge system that the trail goes through and over.

Indian Cave

The Indian Cave is also on the orange dot trail slightly north of Joes Cave and features a wide overhang that you descend down to see as the path skirts round it.

Peter H Borgemeister Trail

Just to the west of the Westwoods area is the Peter H Borgemeister Trail which ambles north south through a stunning glacial erratic boulder field I once dubbed ‘land of the giants’ because it made you feel so small. This is also well worth visiting.

Summary

The Westwoods is run by the Guilford Land trust and has a total of 39 miles of networked trails in 1200 acres near Guilford in CT. It contains the biggest variety of features I’ve seen in CT including salt marshes, lakes, waterfalls, rock formations ( and various features to squeeze or walk through) an Old Leatherman Cave, various other caves and continues to be one of my favourite spots in all of Connecticut for woodland.

Parking Info

Dunk Rock Road Parking northern section

Water Street Southern end parking