From Little Rock to Big Rocks
Constance Baker Motley Preserve, Chester
October 2026
Chester is a lovely riverside town. Most of us are aware of the downtown core of restaurants and art galleries, but outside of that, who really knows Chester? Especially the western half of it on the “other side” of Route 9?
The town is largely covered by the Cockaponset State Forest, but hidden among the trees are at least three retreat centers of varying levels of woo-woo-ness. (The GROVE, The Sound Retreat, and the Guest House Retreat if you’re into that stuff.) There are strange goings-on in the Chester woods.
There’s also the Constance Baker Motley House and Preserve, neither of which is remotely strange, but the area is relatively remote. Motley was a Black civil rights activist, prominent lawyer for the National Association for the Advancement of Colored People (NAACP), and first woman and first Black woman chosen as borough president of Manhattan.
She was also the first Black woman senator in the New York State Senate and the first Black woman appointed as a federal judge. She owned a home in Chester since 1965, using it as a weekend retreat and place for respite. Goodness knows that woman needed some well-deserved respite. It still stands across the road from the Preserve as a private residence on the Connecticut Freedom Trail.
With so much state land in Chester, the local land trust hadn’t had much to work with until the parcel here was purchased in 2016 from the Motley family trust. Since then, the Chester Land Trust has added a parking area, kiosk, informational signage, and a picnic table. It’s a nice spot to learn some important history and then to hike!
The trail here is called the Little Rock Nine Loop Trail. “Little Rock” refers to a landmark case Motley litigated in 1957 in which she represented the Little Rock Nine school children as they fought to integrate Little Rock Central High School in Arkansas. It’s important to note Motley’s legacy, and that was an incredibly important case, but still… the fact that the name was chosen because this trail has some rocky stretches is… a bit of a stretch.
But that’s fine. I’ve been known to stretch a pun or play on words with my page titles on this site pretty much on a daily basis.
A trailhead sign claims this trail is half a mile, but while it’s not challenging, I’m pretty sure that it is a little bit longer than that. I walked the loop counter-clockwise, though I think it might be a slightly better experience going the other way. (And I think the trail designer thinks that as well, since he put the explanation of the trail’s name at what would be the beginning of a clockwise loop.)
These are typical lower Connecticut river valley woods. Maple, beech, oak, and ash with a mountain laurel understory. In a short while, the trail climbed to the ridgeline but not without a fun “warning” sign first:
Don’t be scared. It is not a long or steep climb at all – the picture above is more or less the entire climb. I don’t know the thinking behind the hot pink blazes for this trail, but it is certainly unique. I can’t say I’ve encountered too many hot pink trail blazes in my decades of hiking.
Once atop the ridge, the trail straightens out and gives hikers a view of a rockface across a little ravine. Someone has done that thing here where they’ve created artistic rock “sculptures” of a sort. Like here, where they’ve placed sticks between the split rock layers and built a little sculpture:
They’ve also left a turquoise painted rock at each “installation” as a sort of calling card. I know the purists are against any sort of manipulation in the woods and will knock them down and beg people not to create them. And I get that… I do. But they’re also kind of cool and as long as only natural materials are used (painted rocks aside), I don’t think it’s the worst thing in the world.
The Trust has placed a bench on top of the hill for your weary needs, just before an abrupt 170-degree turn to begin heading back to the parking area. This next stretch of the trail caught me by surprise.
There’s another ravine on this side of the ridge, more defined than the eastern one. Not only that, but the trail travels beside a fairly imposing cliff and takes hikers through some mildly precarious overhangs and down some stone steps – built by the trail creator, Bill Myers. For about 30 feet, this little woodland Chester trail is like a real trail on a real mountain somewhere. Cool.
Once to the bottom of the hill, the trail levels out and makes its way back to the parking area.
This is a unique property because of its historic connection to one of the leading lights of the Civil Rights movement. If you find yourself in the forgotten half of Chester and have some time before your drum circle therapy or whatever, you should check this place out.
CTMQ hikes Chester Land Trust Trails
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