Windsor Trail to Mt Ascutney

The Windsor Trail begins at a small parking area off Back Mountain Road near the town of Windsor and climbs steadily toward the summit of Mt. Ascutney. The route follows a well-marked footpath through classic New England hardwood forest, with moderate grades at first that become more strenuous as elevation increases. At a short distance from the trailhead, hikers pass Gerrys Falls, a small but scenic cascade that flows reliably in spring and after rain. Beyond this point, the trail climbs more steeply, weaving through stands of maple and beech with occasional rocky steps. At higher elevations, the forest begins to thin and patches of exposed granite lead to the open summit. The final stretch offers sweeping views north toward the White Mountains and east over the Connecticut River Valley. This route returns along the same path, providing another look at the trail’s diverse terrain and seasonal foliage. Mt. Ascutney is a rewarding destination for day hikes in southern Vermont, especially in late September and early October when fall colors peak.