- Willis Trail: Ledges on red trail. Willis Trail and Stockmal Trail (challenge #2 below) can be done in the same trip. These two interconnected trails are relatively new and lightly used. Click for Trail Map.
One reason these two trails are in Level 3 is the parking and trail access. There are two options for parking, and in both cases you need to be very careful about traffic whizzing down Leavenworth Road.
The closest parking is a little pull-off (GPS address 361 Leavenworth Road) on the north side of the road at the gas pipeline crossing, near the Stockmal trailhead. The other option is to park at the main lot for Nicholdale Farm on the other side of the road and to the east (#324 Leavenworth Rd).
If you choose the latter, follow the dark blue blazes of Nichols Trail west, parallel with the road. When you arrive at a blue & white blazed connector trail leading to Leavenworth Road, cross there where the sightline is good. Then walk west down the edge of the road a short ways to the Stockmal trailhead.
Follow the white blazes until you see the red blazes of Willis Trail. This is a semi loop, so you can do it in either direction. If you opt for the first junction with Willis Trail, continue up the hill and you'll eventually come to a spot where trail starts to descend down a steep ledge. That was a tricky section of trail to build and it's dug into the side of the hill in places. Take your photo anywhere along the ledges. The trail continues down the hill and reconnects with Stockmall trail. - Stockmal Trail: Trail end marker. See challenge #1 (Willis Trail) for map and parking description. Follow the white blazes all the way to the very end. Two sideways blazes indicate "the trail ends here." Get that symbol in your photo.
We are hoping to extend this trail some day to a good chunk of open space on the other side of the river. Doing so would but it would require crossing Means Brook, which floods terribly.
This area is usually very quiet, with no sound of traffic from nearby roads. When berries are in season, you may hear the anti-bird cannons being fired at nearby Jones Farm. - Birchbank Overlook. This is a really nice hike to a wonderful overlook, no matter how to choose to get there. Click for Map. If you want to do a Wandering Goat Trifecta, come in from Indian Well at the beach access trail, head north on the blue-blazed Paugussett, and pick up challenges #6 and #7 (Burritts Rocks) on your way. That's a nice hike similar in character to the Appalachian Trail in Northwest CT.
A less rocky way to get there is via "Mark's Favorite Hike." You'll know you're at the overlook when you have an unobstructed view of the Housatonic River. A trail register is nearby, but during the pandemic, use precautions when touching common surfaces. - Indian Well Overlook. This is one of the very best overlooks in Shelton. It's on Tahmore Trail, so you could combine this with challenge #5, "Top of Tahmore." There are multiple ways to get there. Click for Map. You can park in the off-season lot for Indian Well located across the street from the main beach entrance, or park at the beach if it's open (no charge for Connecticut residents to park).
Take the white-blazed access trail up the big flight of steps and continue up the hill to the blue blazes, where you'll take a hard left and keep going up the hill. That will connect with Tahmore Trail, a loop with blue/yellow blazes. Take the loop clockwise and you'll be at the overlook in a few hundred feet. Continue around the loop if you want to get challenge #5, Top of Tahmore. - Top of Tahmore. See challenge #4, Indian Well Overlook, for map and parking. Tahmore Trail is a 1.0-mile loop on conservation lands owned by the Shelton Land Trust. The most direct access is at the end of Tahmore Place, a cul-de-sac. For a longer, more challenging hike, come up from Indian Well. Your choice.
However you do it, continue along the loop until you get to the very highest point in elevation. It's a rather open hill top that has seasonal views of the river through the trees. This part of the trail was recently rerouted to the hilltop, so some parts of the trail tread are not packed and worn yet. - Burritts Rocks: Border Brook - border of Indian Well/Birchbank. The next two locations are remote, and accessed via the blue-blazed Paugussett Trail. Do not do these two if it's wet out, because there is a lot of potentially slippery mossy rock to navigate. These two challenges are located in the Birchbank Mountain Open Space, and can be reached from the north or south. For purposes of this challenge, directions are given from Indian Well.
Park at the off-season lot located across the road from the main Indian Well State Park beach entrance. Go up the big stairs on the white-blazed access trail. Turn right to follow the blue-blazed Paugussett Trail northbound. After an easy half mile, you'll cross "Blowdown Brook," a scenic little brook, then start up a long hill as the trail is forced up and around the long boulder field known as Burritts Rocks.
At first the rocks are further down the hill and out of sight, but as you progress up the hill, things start to get rockier. At the top, the trail levels off for a bit where it squeezes between the steep hill on the right and some houses on the left. It then descends into a little rocky valley that's bisected by "Border Brook." Just before the brook, you may notice yellow boundary paint on some trees, and at the brook there will be a little metal marker on a blazed tree for City of Shelton Open Space. Take your picture in there. - Burritts Rocks: The Cave Boulders, Birchbank Mtn. Continue north on the Paugussett Trail from challenge #6 (Border Brook). Go up the hill past the sign board for Birchbank Mountain. Before you know it, the trail will be a jumble of boulders. That's why we call it "The Boulders." You'll need to use your hands to get up and around them.
Immediately after The Boulders, you'll cross a narrow clearing for a water pipeline that goes straight down the hill; you might be able to see the Birchbank parking area at the bottom of it. A short easy section follows before you're confronted with lots of ledge and some very large boulders. We call these "The Caves," although they aren't true caves -- just some overhangs and nooks created by the boulders. There's the Bear Cave on the left as the trail takes a sharp switchback to the right. A bit further on, you'll find a huge boulder, the size of a garage. Take your picture there.
If you feel like exploring, there's another little cave on the far side of this boulder. After you take your photo, you might want to continue through the rocks to the Birchbank Overlook, or save that for another hike. - Paugussett Trail North of Princess Wenonah Drive: Poet Path slates. The Poet Path is a section of the Paugussett Trail that gets little use because it's sandwiched between two road-walk sections of the trail. A few years ago, we fixed up the trail and added some painted slates celebrating the poets after which some nearby streets are named (this part of Shelton is known as "the Poets").
Park at #34 Princess Wenonah Drive (on street parking) and look for some steps going up the hill between houses directly across from a road called "Boulder Path." Follow the blue blazes up up up the hill. The trail curves back and forth within the 20-foot accessway as best it can. Eventually the trail turns right and you'll stop climbing. There are still some ups and downs -- no problem for a goat, though.
Soon you'll start seeing painted slates bolted to trees. You may also see some painted rocks on the ground (this is a good place to leave painted rocks, if you're into that sort of thing). Find the yellow slate that has a quote from Henry David Thoreau, and take your photo there. If you keep going up the trail, you'll get to Webb Mountain in Monroe. - Paugussett Trail at the Overlooks: The ruins (between Sinsabaugh and Rt 110). The blue-blazed Paugussett Trail gets very little foot traffic in the sections between Shelton Lakes and Indian Well. The section just south of Rt 110 runs through a large chunk of peaceful open space but gets very few hikers because it's not easily accessible from a nearby parking lot. You could park at Indian Well and take the blazes southbound, but then you need to cross Route 110, which is a challenge. Or you can reach this area heading northbound from the Shelton Lakes end and spot a car at Indian Well.
From the end of Mayflower Lane, follow the blue blazes northeast and then northwest, gradually downhill towards Indian Well. About 0.3 mile from the end of Mayflower Lane, there are some low stone ruins abutting the trail on the left. No one seems to know what this used to be -- maybe a barn. Odds are that all the trees were cut at the time, and there would have been an amazing view of the river.
If you are coming in southbound from Indian Well, the ruins are 0.3 miles from Rt 110. - Paugussett Trail: Nells Rock Tr overlook rock formation. This site is on the south end of Shelton Lakes off Buddington Road (click for map). There are many ways to get there. For the challenge, consider parking at the southern terminus of the Paugussett Trail, located at #179 Buddington Road.
Follow the blue blazes northbound, passing under the powerlines and continuing on, until you reach the junction with white-blazed Nells Rock Trail. The Paugussett jogs left briefly to follow Nells Rock Trail, but quickly veers to the right to climb up and around a ledge. At the top of the ledge, you can sit and watch the little wooded valley with Nells Rock Trail running through it below. Take your picture here.
Level 3: Wandering Goat
Shelton's 2020 "Out and About Challenge"
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