Blue Hills Skyline Loop

The Blue Hills Skyline route begins from the Willard Street trailhead near Batterymarch Road in the Milton/Quincy area of Blue Hills Reservation. From the parking area, follow the Skyline Trail west as it climbs into the hills and crosses Wampatuck Road. Stay right onto Crags Foot Path to continue along the ridgeline. At trail intersection 4091, turn right, then shortly after, turn left onto Sawcut Notch Path. Continue a short distance before turning left again onto Pipeline, which transitions into Headquarters Path. Follow this wooded stretch before turning left onto Cedar Rock Path. The route crosses Chickatawbut Road and reaches Chickatawbut Tower, where open views stretch toward the city. From the tower, turn right to connect with Sassaman Notch Path, then turn left to rejoin the Skyline Trail and head northeast. At trail intersection 4155 turn right onto Indian Camp Path, cross Wampatuck Road, and return to the Willard Street lot via the Green Dot Pipeline trail. This moderate to moderately challenging route includes granite ridgelines, steep rock scrambles, and forested sections that require steady footing. Multiple highpoints along the ridge offer scenic views across the Blue Hills and toward downtown Boston.