2024 Marathon Level 2, Hike #4: Indian Well/Housatonic Woods Loop

Indian Well/Housatonic Woods Lollipop Loop
(3.4 mi, 770 ft)

SUMMARY: This is our longest hike of the Level 2 challenge with plenty of hills, although the footing isn't too bad as you wander through Indian Well State Park cross the highway, and loop through Housatonic Woods. Enjoy the popular Indian Well overlook and an optional spur to the falls, then continue north on the Paugussett for some solitude. 

PLANNING NOTES:  Choose a time of low traffic volume! This route crosses Route 110. Use caution when crossing, especially if you have a group with children (most hikers have no problem if it is not busy). The parking area and first part of the trails can become very busy on summer weekends, especially in the afternoon. Early mornings are the best time to take this trek. There is also less road noise. 

north section

south section
(click maps to enlarge)

MAPS: Use our custom Google Map #1 to geolocate yourself while hiking. (NOTE: cell phone service is poor in the parking area but is good at the top of the hill. Load your Google map while your still at home). 

PARKING: Indian Well State Park hiker lot, on the left, directly across the street from the main entrance to the beach and boat launch facility. (Currently, Google Maps will get you almost there if you enter "Indian Well State Park." Just continue down the road a bit further).  If the gate is open, you can also park in the main lot on the right (free if you have CT license plates).  During the off season, this lot can fill up on weekend afternoons if the weather is nice. 

CONDENSED HIKE DESCRIPTION: Head up the stairs on the white access trail located behind the info kiosk. Turn left onto the Paugussett Trail (blue) southbound. At the top of the hill, take the blue/yellow trail about 300 feet to the overlook. Retrace your steps back to the blue trail and continue on blue southbound to Indian Hole Brook. Cross via stepping stones or the roadway. (Unmarked optional spur to the falls is on the right). Continue on blue, crossing Route 110, passing the blue/orange connector on the right. TURN RIGHT onto Woodsend Trail (orange). After 0.5 mile, TURN RIGHT onto blue/orange connector, then LEFT onto the Paugussett. Recross Rt 110 and Indian Hole Brook. TURN RIGHT onto the blue/red Beech Cutoff Trail and follow blue/red all the way back to the car. 

FULL HIKE DESCRIPTION: Head past the info kiosk and up the steps on the white-blazed access trail. Turn left on the blue-blazed Paugussett Trail, heading southbound and up the hill. At the top is Tahmore Junction. Two trails are co-aligned for a few feet, leading to a well-signed tree. From this tree follow the blue/yellow blazes of Tahmore Trail up the hill to the overlook in about 300 feet. 

After enjoying the view, retrace your steps back down to the blue trail, and continue southbound (Veer right, down the hill. Some people find this spot confusing because the trail appears to be heading back north, but it's just temporary). Pass two junctions with the blue/red Beach Cutoff Trail, which you will be taking on the way back. Stay on blue all the way to Indian Hole Brook. 

Cross the brook, either using rocks if the water is low, or take the short blue/white bypass trail out to the Indian Well Road and cross via the old stone bridge. 

Once across the brook, you have the option of visiting the falls by taking a right on the unmarked but heavily used trail that heads upstream. (The falls are best visited during off-times after a good rain. During peak summer season, the falls can become crowded and littered.)

Continue on blue, crossing Indian Well Road and heading through the middle of the meadow, re-enter the woods, pass some ruins, and continue along the toe of the slope. 

Just above this section there is a very old highway running parallel to the trail. This was the original highway before Rt 110 was built. The Housatonic River was tidal back in the day, and there was a major shipyard and port. Farmers in the White Hills brought their produce here. This was the busiest part of what would later become Shelton. 

The trail eventually rises up to follow this old highway a short ways before heading up the hill via switchbacks. Enjoy the view of the pond below and catch your breath before continuing up to Route 110. 

Cross the highway at the blue oval sign for the best sightlines, and continue up the hill on blue. You're now in Housatonic Woods, owned by the City of Shelton. Pass the blue/orange connector trail on the right and then an old stone barn foundation. TURN RIGHT onto orange-blazed Woodsend Trail (if you reach Mayflower Lane, you missed the turn). 

Woodsend Trail follows the grade for a good way, crossing a number of drainage channels, before descending past a green chain link fence on a sewer line. Keep an eye out for the blue/orange Woodsend Connector Trail on the right (0.5 miles from the start of the orange blazes) and follow this trail back to the Paugussett Trail. 

TURN LEFT onto the Paugussett Trail and follow it back down across Route 110 and Indian Hole Brook. Continue on blue until you reach the blue/red-blazed Beach Cutoff Trail on the right. Follow the blue/red blazes, which will briefly rejoin the blue trail due to the steep terrain and then split away again to the right. These blazes will take you back to your car.