Owls Head

The Owl’s Head Trail begins at the Quarries Trailhead on Raptors Lane. From the parking area, the route climbs steadily through mixed hardwood forest before reaching a Owls Head. Shortly after reaching the crest, a spur leads to an open perch with sweeping views across Dorset Valley and the Taconic Range. Returning to the main trail, continue uphill as the grade steepens on rocky terrain toward the summit of Owl’s Head. The final stretch includes scrambling over ledges and exposed rock before topping out on the rugged summit. From the top of Owl’s Head, hikers are rewarded with expansive views east into the Green Mountains and south along the ridgeline of the Taconics. Both the summit and Gilbert Lookout feature cliffs and open ledges, so caution is needed with children and dogs. The combination of forested climbing, open vistas, and challenging terrain makes this a rewarding day hike in the Dorset area, especially during peak fall foliage.