2024 Marathon Level 2, Hike 10: Woodsend Trail

SUMMARY: Our newest trail traverses Housatonic Woods Preserve along the upper slopes of the Housatonic River for a mile before connecting with the Paugussett Trail, which is used to create a lollipop loop. Off-season hikers are rewarded with seasonal views of the Housatonic River Valley. The most dramatic part of this hike is "the Passageway" through a cliff area that rises over Leavenworth Road. 

PLANNING NOTE: There are some sharp drop-offs next to the trail in the area of the Passageway. Most of the footing is good, but there are several unimproved brook and gully crossings. A hiking stick or trekking poles may come in handy.

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MAPS: The full official trail map is here.  Use our custom Google Map #2 to geolocate yourself while hiking. 

PARKING: GPS #50 Woodsend Avenue, which is at the junction with Cynthia Lane. There is a hammerhead pull-off for three or four cars. 

CONDENSED DESCRIPTION: Follow Woodsend Trail (orange) for one mile, ending at the Paugussett Trail (blue). Turn left and follow the blue blazes downhill for 0.4 mile. Turn left onto the blue/orange Woodsend Connector Trail. Turn right onto Woodsend Trail and continue back to your car. 

FULL DESCRIPTION: Head down the orange-blazed Woodsend Trail. You will be following the orange blazes for a full mile. The trail descends the hillside, winding back and forth to prevent erosion, crosses an intermittent stream, and joins an old woods road as it levels out. This old road was used to carry wagons laden with charcoal. The trail deviates from the old road to explore a scenic plateau with seasonal views of the Housatonic River Valley. 

On the right will be a textbook example of an old charcoal mound. There is a central mound encircled by a trench. This is where charcoal was created by slowly burning logs in a low oxygen atmosphere. Skilled colliers would stay with the mound for several days. The charcoal here was probably used in the brass mills that operated along the Naugatuck River. 

Now the trail winds its way up to the Tangerine Squeezer, which marks your entrance into the Passageway.  Squeeze between the orange-blazed tree and a chunk of ledge, and you have entered a different world. There are cliffs both above and below you. Leavenworth Road (RT 110) is at the bottom of these cliffs, and the road can be noisy. During the offseason, you can see the highway as well as Indian Well Road and then the Housatonic River, all parallel with each other as they squeeze past these cliffs.  

The constricted Passageway is not long. Soon the landscape opens up before you. The trail switchbacks down the steep hillside and then crosses a boulder field and a seasonal brook. 

You are now in the southern section of Housatonic Woods Preserve and will soon begin the loop section of your hike. Stay straight on the orange trail when you pass the blue/orange Woodsend Connector Trail on the left (you will return on that trail). Continue gradually up the hill for a good ways and then level out as the trail passes through an area that was an overgrown pasture not that long ago. There are lots of vines and thorny barberry, and the trail crosses several drainage gullies.  

The trail will veer to the left as the buildings of Sinsabaugh Heights come into view (an unmarked access trail heads off to the right), and then continues through the woods below the senior housing before coming to an end at the Paugussett Trail. If you turned right, you would soon arrive at Mayflower Lane and could continue on to Shelton Lakes. For this hike, TURN LEFT and follow the blue blazes down the hill. 

Pass the stone foundation of an old barn and several intermittent brooks and drainage gullies (larger than they were up above). After 0.4 mile, with the sounds of Route 110 getting closer, TURN LEFT onto the blue/orange-blazed Woodsend Connector Trail. This brief connector will take you back to Woodsend Trail. TURNING RIGHT onto Woodsend Trail will bring you back to your car in half a mile.