1.6 Miles Easy
Blue Hills Reservation
Near Milton, Massachusetts
This 1.6 mile loop hike at the Blue Hills Reservation in Milton, Massachusetts covers a small portion of the Skyline Trail (blue blazes), part of the Dark Hollow Trail (green blazes), and part of the Headquarters Path Trail.
From the main parking lot, across the street from the state police station, take the trailhead for the Skyline Trail and follow the blue blazes until you reach the top of Tucker Hill and see an intersection with green blazes. Follow the green blazes north, as this is the Dark Hollow Trail. The Dark Hollow Trail will lead you downhill from Tucker Hill toward Chickatawbut Road. Once you reach the part of the trail where Chickatawbut Road connects with Hillside Road, you'll hop directly onto the Headquarters Path Trail, which leads directly back to parking to complete the loop.
Views: There isn't much for views on Tucker Hill, but there's a small lookout-type area.