Click the red flag above to locate trailhead parking
Overview & Map
Shepherds Trail This diverse trail includes a variety of ecosystems from lowland wetland swamps, woodlands and small meadows to upland forest and rocky exposed outcrops. The trail is one of our most demanding with several short, steep sections and rocky areas that can be slippery when wet or icy.
Category: Fairly difficult due to steep climbs over rocky areas.
Start: Trailhead at the corner of Shepherds Trail and Summer Hill Rd.
Distance: About .5 mile, one way.
Parking: Near the trailhead on Shepherds Trail Rd.
What to look for on Shepherds Trail
From the trailhead, descend the short drop into the forest of red and sugar maples. Scattered among these species are occasional stems of black birch, sassafras, hickories and tulip poplar. Soon, the trail crosses a small stream that drains this lowland forest and the wetland to the east. Turn sharply north and then enter a series of small meadows created years ago in an unsuccessful attempt to create a wetland replacement for one destroyed by development. These openings with their mixtures of grasses, mosses, lichens and swaths of herbaceous growths of goldenrod, blackberry, cinquefoil sumac, queen Ann’s lace and many others, together with seedlings of several tree species, add much diversity of habitat for a number of birds and mammals. Deer and rabbits feed here as evidenced by winter trails and browsed shrubs and saplings and hawks can often he heard and see as they cruise these openings for prey.
East of the meadow, the trail enters a wetland forest that borders a well-defined red maple swamp. The shallowness of the water table here is attested to by the uprooted trees and pockets of standing water during wet times.
Just beyond a small bridge, swing right to encounter a magnificent curving stone wall. Why this wall was built, presumable by Rueben Johnson, is now a mystery. Mr. Johnson, who settled here in the mid-1700s, owned land from Summer Hill Rd. east to Buck Hill. Shortly on, the trail turns east across a stream that drains the wetland. Dry in the summer, the stream carries a sizable flow in the winter and spring. Note the numerous yellow birch trees here—a sign that this area is cool and moist. Near the rock outcrop, the trail passes through a sense stand of ferns and by an old charcoal mound. Rueben Johnson’s journal records selling the “coal” made on his land.
Turn left at the foot of the outcrop and on through a young stand of mixed hardwoods whose composition (sugar maple, hickory, black birch, red and white oaks, and several quite large black gums) indicates that the soil here is deeper and better drained than in the wetter forests just encountered. An understory rich in sugar maple saplings suggests that this shade-tolerant species will dominate this stand in the future.
Soon the trail joins an old woods road and heads uphill, turns right, and angles up to the rock summit. In the winter there are good views of Legend Hill to the west and of the valley below. Just below the face of this outcrop, and out of sight, openings created by fractured rocks form den sites for fox—marked by tracks and scat.
Descend to a small saddle and continue along the base of the next outcrop to where year-round seeps create spectacular falls of ice along the cliff face in winter. Just beyond, climb upward and continue east through a passageway created when several trees, perched on the sheer rock, blew over in a storm. Higher up near the ridge top, large hickories and chestnut oaks occur along with a few white pines and red cedars that add some winter green.
Descend steeply to mid-slope and cross a ravine through which water flows freely in wet times. In winter, ice flows develop here and water can be heard trickling beneath the ice sheets. Ascend steeply passing large old chestnut oaks to near the crest. Follow the trail carefully along the moss-covered rocks that can be slippery when wet or icy. Finally, pass through a young oak stand, whose multi-stemmed character reveals an origin from stumps of larger trees cut a few years ago, and emerge into an opening with excellent views to the south of Long Island Sound.
Upslope and to the east, the trail reaches the highest overlook. Unfortunately due to the large number of dead Hemlock trees, the trail is closed beyond this point. To return to your car, retrace your steps to return to the trailhead.
PLEASE NOTE: Hunting, camping, fires, cutting trees or vegetation, horses, and motorized vehicles are all prohibited on Madison Land Conservation Trust property. MLCT trails and properties are for hiking only. Dogs are allowed, but must be leashed. Please pick up all animal waste.