North Skyline Trail is a hiking and biking trail in Milton, Massachusetts. It is 1.3 miles long and begins at 243 feet altitude. Traveling the entire trail is 2.7 miles with a total elevation gain of 1,074 feet. Near the trailhead there is a parking. Wolcott Hill (elevation 433 feet) and Hancock Hill (elevation 509 feet) can be seen along the trail. The trail ends near the Eliot Tower viewpoint. There are also an information map and a picnic site near the end of the trail.