Chester Memorial Trail to Haystack Mountain

The Colby M Chester Memorial Trail begins off Waite Road near Pawlet, Vermont, and climbs gradually into wooded hills. This route follows a moderate ridgeline ascent through mixed hardwood forests with intermittent clearings and seasonal runoff. Early on, hikers pass through low elevation woods before reaching a ridgeline offering wide views of the Taconic Mountains. From here, the trail continues along the ridge with short climbs and occasional muddy stretches—especially after rain or during spring thaw. Along the way, hikers can expect shaded forest walking, opportunities for birdwatching, and seasonal wildflowers. Wildlife is common in the area, and ticks can be active in warmer months. Snowshoes are useful in winter, and the trail remains open year-round, though conditions are most favorable from late spring through fall. The high point offers rewarding views across Vermont’s rolling western terrain.