Hiking in Northwest CT

Starting at Lake Waramaug, I will be talking about things to do and see and move out from there to neighboring areas.  Today I’ll be highlighting hiking in the area.

New Preston Pinnacle

This is about a 2 mile hike that will bring you through a typical New England woodland and up to a huge outcrop at the top of the mountain.  There are two approaches to the pinnacle; one on each side of the mountain.  The original trail begins only yards away from my hot dog stand on June Road.  There is a very small parking area up on June Rd. with a marked fence announcing the trailhead.

The trail on the other side of the mountain begins just off Christian St. off Rt. 202 in Macricostas town park.  On this trail there are two ways to go.  Once on the main trail, it splits to a longer, easier way, or a shorter, steeper path.  All trails are marked in yellow.  About halfway up this side, there is an overlook with views to the east.  On the way, the trail is marked through the first bog with plaques explaining the foliage, trees and other things of interest along the way.  To get to the main trail, you park at the red farmhouse on Christian St. The trail is marked from there.  You first cross a small bridge and boardwalk.  Then you follow the border of a great field.  You will pass a side rest point with a bench along the river (Bee brook) and not much farther you’ll turn left onto the main trail. About 500 feet past that turn, there is another short trail to a lookout stand at the beaver pond.  Maps of all the trails are usually available at the trailhead.  The great reward is at the top of the pinnacle; an awesome 360 degree view with Lake Waramaug to the west, New Preston, Marbledale and Northville to the south, Washington to the east and MA to the north.  Enjoy!


From the Pinnacle, you can look to the north and when the leaves are off the trees, you may be able to see the old fire tower at Mt. Tom state park located in Woodville, CT.  From the park there is a trail to the top and the tower is open to visitors.  It, too, provides an excellent 360 degree view overlooking Mt. Tom pond, which is especially pretty in fall foliage.  This one is about a 20 minute to half hour hike, depending on the individual.  There are ruins along the way of an old house that once stood there in the woods.

Lover’s Leap         

In New Milford we have a brand new State Park just off Grove St. called Lover’s Leap.  Very rich in history, indian lore and unique structure it’s a must see.   The plaques at the trailhead near the old bridge tell a good part of the story, but there is so much more to it.  The old bridge was re-furbished a few years ago and used to be the main road.  It was preserved as an historic landmark because of it’s unique lenticular structure.  There are only a few in existance and two of them are in New Milford.  The second is upstream in the Boardman district of town along Rt. 7.  There are hiking trails throughout “the leap” and one leads to the ruins of the old Hurd Castle and tea house.  Both burned down not long after the death of Katherine Hurd in the mid-1970’s who left the estate to the state for a park.   Chief Waramaug, who the lake is named after, is said to be buried near the fireplace of the old castle.  His tribe lived in New Preston around the lake in the winter and they summered over at Lover’s leap.  The Housatonic river becomes Lake Lilinonah below the lover’s leap gorge, and is named after the Chief’s daughter.  It was she who drowned in the river after thinking her English lover had betrayed her and left for England never to return.  He returned just as her canoe went over the falls.  He dove in to save her and they both were drowned.  Hence, the name Lover’s leap.  From the old bridge, you can hike a very short distance to “The Leap” and get a breath-taking view of Lake Lilinonah from the top of the cliff.

Hidden Valley

About four miles from our Now well known lake, we have a very lovely hiking area known as Hidden Valley.  It’s part of the Steep Rock reservation of Washington.  Literally “hidden” off Rt. 47, access is on both sides of the Shepaug River. There are unmarked trails on the Washington side of the river which will eventually lead to an old quartz mine.  If you don’t want to go that far, you will come to a footbridge where you can cross and return to the parking area on the other side of the river. There are other trails through the woods for the hearty and adventurous.  I only say that as I got lost once and found myself about 5 miles up the road.  Take a GPS with you as most of the trails are unmarked.