Blue Hills Loop Hike

Blue Hills Loop Hike

1.6 Miles Easy

Blue Hills Reservation
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.


Dogs (leashed)

Get Directions

42.21389, -71.093399
N 42º 12' 50.004" , W 71º 5' 36.234"
Map Type:


229 '
Elevation Change
266 '
Elevation Gain
243 '
Elevation Loss

Photo Albums

Other trails at Blue Hills Reservation

Trail Name
2.0 Miles
Blue Hills Loop Hike
1.6 Miles

Total Miles

1 Trip Report

1.6 miles
added on 07/2015