Late Fall – Hemlock Hills

The Hemlock Hills

Hemlock Hills is a Ridgefield open space. I have been aware of it for a few years. It is often lumped together with Pine Mountain open space, with which it is contiguous. Both spaces abut Bennetts Pond State Park too, creating an unbroken natural area well-endowed with hiking trails.

Fall colors in a Hemlock Hills ravine

Fall colors in a Hemlock Hills ravine

I have hiked Bennetts Pond and Pine Mountain several times and count their highlights among my Fairfield County favorites. Bennett Ponds themselves (the wetland is usually mapped in the plural, although to me it has always appeared as a single body of water) are atmospheric—shallow, reedy, alive with wildlife and light. Pine Mountain—wooded—rises steeply behind the ponds, and on the mountain’s west side one of the biggest views in the County is on offer.

On my Bennetts Pond and Pine Mountain outings I have likely strayed into a corner of Hemlock Hills, but otherwise the Hills have been terra incognita to me. Earlier this month, I set out to change that.

But where to start? The Hemlock Hills map showed five trailhead parking areas, not bad for a tract of just 421 acres. I decided on the trailhead at the end of North Shore Drive because it lay beside Lake Windwing, which might be pretty and had a curious name. I parked at the lake at 2 p.m. on a Saturday and roamed the Hemlock Hills until sunset. It was a hesitant, half-oriented hike, a first taste of a new destination.

I found that Hemlock Hills offered small but abundant pleasures. First, there was little Lake Windwing, reedy and undeveloped at its eastern end, a brook flowing out over a low weir. (As for the lake’s name, check out Jack Sanders’ Ridgefield Names website. I am pleased not to be alone in having thought of it as Lake Wingding!) Hemlock Hills also served up an imposing rock outcrop, pretty wetlands, a huge boulder or two, and a ravine that would befit a much wilder landscape. I saw all this on a chill late-autumn day, when yellow and copper leaves still clung to the small trees and the sun sank in a warm orange glow.

Many hikers, myself definitely included, like to trek with an objective. We’re not very good, in truth, at wandering. An objective gives form and spurious purpose to the outing. And if the goal can be some impressive natural feature, so much the better (“Our hike today is Bearscat Bald and back”). I had wandered Hemlock Hills and enjoyed its small scenes. Now I wanted to return with an objective and a plan.

The objective could only be the big view from the Charles Ives cabin site on the west side of Pine mountain. The site is in Pine Mountain open space, but I’d plan a route through Hemlock Hills to get there. I marked out this route on my trail map, taking care to pass close to swamps, to traverse the ravine, to walk the edge of Pine Mountain where there is a glimpse down to Bennetts Pond. Plans are crazy and reassuring in about equal measure.

I returned to Lake Windwing five days after my first visit, on a freezing, gray morning portending the coming of early snow. My route to Pine Mountain delivered some of the scenes I had anticipated, but not others. There was a craggy, disorderly cliff; a lonely glacial boulder; and a brook running among mossy stones. But the swamps marked on the map did not show, at least not as the bright clearings in the wood I had hoped for.

I came down almost to the northwest end of Bennett Ponds, climbed the steep 500 feet onto Pine Mountain, and turned west for the Ives cabin site. A good hike objective should be a place you want to linger a while, and in this the ledge at the Ives site did not disappoint. Its view is a south-facing 180 degrees, over the treetops of miles of undulating forest, apparently empty but far from being so. The most prominent hump in the forest, two miles due south, is the high point of Seth Low Pierrepont State Park (like Pine Mountain, about 1,000 feet in elevation).

I had planned to return to Lake Windwing on the red-blazed trail. But plans, comforting as they are, are also meant to be torn up, and when the cold moved me on from the ledge, I took the yellow trail. It guided me off Pine Mountain and into the ravine below, a place whose rough contours and wild mood are not entirely of Fairfield County.

At the end of my hike, I went down to Lake Windwing. Thin, clear ice had formed along its edge. Back home, I built a fire, and soon snowflakes filled the air. The next morning, I had to find the snow shovel. Winter!



PARKING North Shore Drive, Ridgefield, CT (GPS: 41.344283, -73.511164).
DISTANCE 5-6 miles at a rough estimate.
DURATION 2¾ hours.
MAP Available at some trailhead kiosks and online (, Conservation Commission, Catalog of Open Spaces).
ROUTE Use any Hemlock Hills trails, but climb Pine Mountain on the red trail nearest Bennett Ponds and approach the cabin site from the east.
WHAT TO TAKE In cold weather, gloves, warm hat, and layers. Water and snacks.
Charles Ives cabin site -- Pine Mountain

Looking down from the Charles Ives cabin site — Pine Mountain