Shaped like a Y, this 4.1-mile rail-trail connects Marblehead, Salem and Swampscott. From the trail junction in quaint Marblehead, one branch meanders through conservation areas and past harbor overlooks to Salem, notorious for its 1692 witch trials. The second branch offers a longer route heading toward Swampscott through Marblehead's residential areas, offering a more local look at this seaside community. The intersection of Bessom Street and Roundhouse Road in central Marblehead marks the apex of the trail, and a good starting point.
Follow the sandy path on the west side of Bessom Street 0.25 mile to the trail junction beside a fenced utility yard. Time to choose: to the right lies Salem, while the left branch leads down the coast toward Swampscott. The branch toward Salem begins with a sandy surface and soon enters Hawthorn Pond Conservation Area, a 9.8-acre preserve with marshes, ponds, streams and four interconnected nature trails.
Take care as you emerge from the conservation area on West Shore Drive: traffic can be heavy. Up next is Wyman Woods Conservation area, a 33.5-acre mix of wetlands and mature forests that gives way to beautiful views of Salem Harbor. On warm days, trail users can hike down a sandy path to the water's edge for a refreshing dip or stop along the wooden railroad bridge for a particularly inspiring view of the harbor. Entering Salem, the trail crosses State Route 114; use caution at this major artery. Beyond, artistic gates modeled after antique high-wheel bicycles mark the path, and the surface switches to smooth asphalt.
You'll soon pass Salem State College then enter a commercial area. The trail ends at Canal Street. The alternative branch of the trail toward Swampscott also begins on a sand and gravel surface. Crossing Pleasant Street, you'll pass the public high school, where ball fields and playgrounds offer ample open space for a quick stretch or a relaxing break. Students use the route as a commuter corridor. From the high school, the asphalt trail continues along a raised corridor through residential areas, with plenty of paved access roads to Marblehead beaches. The trail ends at the Temple Emanu-El parking lot.
To reach the main trailhead, take State Route 128 to Exit 25 and head south on State Route 114 south to Marblehead. In town, SR 114 becomes Lafayette Street and then Pleasant Street. Follow Pleasant Street into town then turn left on Bessom Street. Just past the shopping center on the right, take your first right turn onto Roundhouse Road. The trailhead is across the street.