Shepards Trail
Description
This trail winds through a mix of forest types, open meadows, wetlands, and rocky outcrops. Along the way, hikers pass old stone walls and historic land features, including a long, well-preserved wall believed to have been built in the 1700s. The path moves between shaded woods and more open stretches with seasonal views of surrounding hills and valleys. In winter, distant ridgelines come into view through the bare trees, adding to the sense of openness. The changing terrain includes quiet groves, stream crossings, and moss-covered boulders. Wildlife is active throughout, especially around the meadows and wet areas. This trail offers a blend of peaceful natural beauty and subtle reminders of the land’s past.
Trail Map
Map Credit: Madison Land Conservation Trust
Difficulty
Difficult
Despite the trail's short length, it features some challenging rocky areas. Starting from the parking area you'll start on some flat easy parts, but once you get to the rocky area there are some pretty steep, narrow, and rocky trails. This trail is especially difficult in rain because lots of the trail is covered in rock.
Pictures
