From the trailhead, the trail descends into a 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.
Just beyond a small bridge on the right is a magnificent curving stone wall built by Rueben Johnson. Mr. Johnson, who settled here in the mid1700s, owned land from Summer Hill Road east to Buck Hill. Shortly on, the trail turns east across a stream that drains the wetland.
Turning left at the foot of the outcrop, leads 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 also suggests that this shade-tolerant species will dominate this stand in the future.
Soon the trail joins an old woods road, 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.
Descending a small saddle and continuing along the base of the next outcrop leads to year-round seeps that create spectacular falls of ice along the cliff face in winter. The trail continues east through a passageway created when several trees, perched on the sheer rock, blew over in a storm.
The trail then descends steeply to mid-slope and across a ravine. In the winter, ice flows develop here and water can be heard trickling beneath the ice sheets. Soon the trail, ascends steeply and passes large old chestnut oaks near the crest.
Following the trail carefully along the moss-covered and through a young oak stand, and emerge into an opening with views of Long Island Sound to the south.
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. At this point, retrace steps to return to the trailhead.
From the Route 79 round-about, exit at North Branford Road (Route 80) going towards Killingworth. In approximately 1 mile, turn right onto Summer Hill Road. After a 0.25 mile turn left onto Sheperds Trail. The entrance will be on the right. The trail is located at 438 Summer Hill Road, Madison, CT. Parking is located near the trailhead on Shepherds Trail Road.
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