Devil’s Den Preserve (Weston, CT)
Directions to trailhead
From the George Washington Bridge, take I-95 to the Major Deegan Expressway north, which becomes the New York State Thruway. Take Exit 4, proceed east on the Cross County Parkway, and continue on the Hutchinson River Parkway north. Beyond the intersection with I-287, where I-684 begins to the left, bear right to continue on the Hutchinson River Parkway. The parkway crosses into Connecticut, where it becomes the Merritt Parkway (CT 15). Take Exit 42 (Westport/Weston) and turn right at the end of the ramp onto CT 57. Proceed north on CT 57 for 3.8 miles, then turn left to continue on CT 57 (as CT 53 proceeds straight ahead). Just beyond, follow CT 57 as it curves sharply to the right. In another 1.3 miles (beyond the sharp curve in the road), turn right onto Godfrey Road and proceed for 0.6 mile to Pent Road. Turn sharply left onto Pent Road and continue to the end of the road, where there is a parking area for the Devil’s Den Preserve.
This 1,700-acre preserve is the largest nature preserve in southwestern Connecticut. The system used to blaze the trails in the preserve differs from standard Trail Conference practice in that the color of the blaze designates only a category of trail use and does not distinguish one trail from another. Red-blazed trails are for hiking and cross-country skiing; yellow-blazed trails are hiking-only; and white blazes indicate that the trail is part of the Saugatuck Valley trail system. Each trail junction is marked with a signpost that gives the number of the intersection and corresponds to the numbers shown on the map.
From the northeastern corner of the parking area, at junction 21, head east on the Laurel Trail, an old woods road, with red and white blazes. At junction 22, bear right and continue ahead on the Laurel Trail. Just beyond, at junction 23, a yellow-blazed trail begins on the left, but you should continue ahead, following the red and white blazes. The trail descends, crosses a wooden bridge over a stream, then turns sharply left at junction 31.
At junction 32, a side trail on the left leads down to the site of an historic sawmill. After making this short side trip, return to the main trail and turn left. Just ahead, bear left at the fork, then turn left and follow a footpath across the stone dam of Godfrey Pond – a mill pond built in the 1700s. Almost immediately, you’ll reach junction 25, where you should turn right onto a yellow-blazed trail.
Soon, you’ll reach the shore of the pond at another stone dam and spillway. A bench has been placed here, and you may wish to pause and enjoy the view. The trail bears left and descends to junction 26. Turn right here and cross the outlet of the pond on rocks and a wooden footbridge. Continue to follow the yellow blazes as the trail passes between cliffs and reaches junction 27, where you continue ahead, with the pond below on the right.
After crossing an inlet of the pond on a wooden footbridge (with cascades in the stream to your left), you’ll reach junction 30. Bear right, cross another inlet on a footbridge, and continue to follow the blazes around the shore of the pond. When you reach a woods road at junction 34, turn left onto the road, now following red and white blazes.
Soon, you’ll come to a fork at junction 35. Bear left here and begin to follow the Godfrey Trail, a woods road marked with red and white blazes. You’ll be following this trail for the next two miles. In a short distance, after crossing a stream on rocks, you’ll reach junction 36, where a side trail that leads back to the pond begins on the left, but you should continue ahead, following the red and white blazes..
In about a mile, you’ll arrive at the Portable Sawmill site, with an interpretive sign and rusted remnants of machinery from the sawmill that operated at this location from the late 1800s until 1922. The trail now climbs to signpost 39, where you should bear right and continue to follow the red-and-white-blazed Godfrey Trail.
In another half mile, you’ll reach junction 64, where you continue ahead, now following the Pillars Trail. After crossing a footbridge, you’ll come to junction 63. Here, you should turn left, leaving the Pillars Trail, and begin to follow the Dayton Trail, marked with yellow and white blazes. (Note that yellow blazes are also used in this area to mark the boundary of the preserve. Take care to follow the trail, which has a well-defined footpath.) The trail goes by a cliff and climbs to junction 58. The Deer Run Trail, which begins on the left, will be your return route, but for now, bear right.
Almost immediately, you’ll reach junction 56. Turn right here and continue on the Great Ledge Trail. Soon, you’ll arrive at a rock ledge with a view through the trees of the forest below. This is the first broad viewpoint you’ll encounter on the hike. Just beyond, another rock ledge to the right of the trail offers a less obstructed view of the same forest. You might want to pause here to take in the view, but a more spectacular viewpoint is just ahead.
After descending a little, you’ll pass on the left a small monument (painted yellow) with the letters “W” and “R” (signifying the boundary between the towns of Weston and Redding) and reach junction 59. Continue straight ahead. When you come to junction 60, turn right, now following only white blazes.
In a short distance, you’ll come out on a rock ledge with a panoramic view over the Saugatuck Reservoir. Continue ahead on the white trail, and you’ll soon reach yet another viewpoint (from a rock ledge on the right), with an even broader view of the reservoir. This is the “real” Great Ledge, and you’ll want to take a break here and enjoy the view.
The trail now descends rather steeply for a short distance, then continues ahead and soon reaches junction 62. Continue ahead, and almost immediately you’ll reach junction 83. Turn left here, now following yellow blazes, and in a short distance pass through a gap in a stone wall and reach junction 61. Turn left, now following yellow and white blazes, and you’ll soon arrive at junction 59. You may recall this location, as you were here previously. Turn right and retrace your steps to junction 56 and, just beyond, junction 58.
Turn right at junction 58 onto the yellow-blazed Deer Run Trail. When you reach junction 55, turn left to continue on the Deer Run Trail, now blazed red, which descends steadily through mountain laurel thickets. After crossing a stream, the trail ascends gradually to junction 54. Turn right and begin to follow the Bedford Trail, a wide woods road that is also blazed red (with some old white blazes).
You’ll pass junction 52, where the Moller Trail begins on the right. In another mile, you’ll reach junction 49, where the Donahue Trail begins on the right and the road changes its name to the Den Trail (although this is not indicated by a sign). In each case, continue ahead on the woods road, marked with red blazes. The Ambler Gorge Trail goes off to the right at junction 44 (with a large wooden sign on the right), but you should continue ahead on the main woods road, which descends steadily.
After crossing a footbridge over a stream, you’ll reach junction 10. Here, you should bear left and continue to follow the wide road, which is now known as the Pent Trail. You’ll recross the stream on a wooden bridge and proceed ahead on the road, passing junctions 9, 8 and 7. Note that, between junctions 7 and 6, the trail is blazed yellow. The map shows this section of the road as a thin line, but that is because the road descends very steeply at this point and is therefore not suitable for cross-country skiing. The McDougal Trail (West and East), shown on the map with thicker lines, is actually a narrower route.
Continue to follow the road past junctions 6, 19, 5, 4 and 3 until you reach the parking area where the hike began.