Ghosts, curses, and even the occasional headless horseman are not just Halloween fodder. Although late October is their time in the spotlight, they haunt trails throughout the Northeast year-round. For generations, ghoulish legends have been passed down by storytellers and witnesses alike, spooking hikers along the way. Even if you’re not a believer, these tales can still teach you something about past settlers, conflicts, and tragedies that took place where you hike today.
One of the most popular peaks in the White Mountains, Mount Chocorua can be climbed via the Piper Trail, which begins on Route 16, crosses the Chocorua River, and ascends along ledge and stone steps with views to the north, east, and south. Once atop the summit you’ll be at the site where Sokosis Chief Chocorua—distraught over the death of his son—supposedly cursed the surrounding area and its settlers. Many strange and tragic happenings have been attributed to the curse.
Distance: 4.3 miles one way
Info: White Mountain Guide, 28th ed. (AMC Books); Haunted Hikes of New Hampshire (Marianne O’Connor, PublishingWorks)
In the center of Cape Ann is a 3,600-acre boulder-strewn forest with a colorful history that includes pirates and witches. So named for the pets left behind as residents gradually moved toward the coast, Dogtown was also home to Tammy Younger, an alleged witch who threatened to curse passersby. Follow Dogtown Road from the Cherry Street parking area to Dogtown Square (.75 mile), where a ghost town of cellar holes remains. Connect to the Babson Boulder Trail to loop back to Dogtown Road.
Distance: 2.5-mile loop
Info: Essex National Heritage Area
Berlin to Meriden, Conn.
The Black Dog of West Peak is said to wander Connecticut’s Hanging Hills, and for years has received the blame for accidental deaths in the area. The Metacomet Trail passes through the canine apparition’s stomping ground, and can be accessed from a trailhead on Summitwood Drive in Berlin. Follow the blue blazes to the west and take the trail over both West Peak and East Peak. Turn around when you reach Edgewood Road and return the way you came. Be careful, however: One sighting of the black dog is said to bring joy, a second misery, and a third death.
Distance: 8.3 miles round trip
Info: AMC’s Best Day Hikes in Connecticut (AMC Books); Connecticut Walk Book: East (CFPA)
Rockefeller State Park Preserve
Pocantico Hills to Sleepy Hollow, N.Y.
Few tales have captured the American imagination like Washington Irving’s “The Legend of Sleepy Hollow,” set just 25 miles north of New York City. From the Rockefeller State Park entrance follow the Old Sleepy Hollow Road Trail for about .75 mile. Take a left on the Pocantico River Trail. Another .75 mile will bring you to the Old Croton Aqueduct Trail; go left toward Sleepy Hollow (1 mile away). Irving is buried in the adjacent Sleepy Hollow Cemetery, and just down Route 9 is an 18-foot-tall statue of his Headless Horseman chasing Ichabod Crane.
Distance: 5 miles round trip
Info: Friends of the Old Croton Aqueduct
New Jersey Pine Barrens
Decades of eyewitness accounts boosted the legend of the Jersey Devil to such a stature that it was named the state’s official demon in 1938. The devil is said to be a biped with wings and hooves that haunts the 1.1 million-acre Pine Barrens of South Jersey. The Batona Trail forms a 50-mile spine through the barrens, providing ample devil-spotting opportunities. Start your hike near the Carranza Memorial in Wharton State Forest and head north. The fire tower atop Apple Pie Hill—your turn-around point—provides one of the best views available of southern New Jersey and the Pine Barrens.
Distance: 9 miles round trip
Info: New Jersey Pinelands Commission; Pinelands Preservation Alliance
Hawk Mountain Sanctuary
The Lenni-Lenape tribe considered this land sacred in the 1700s. An innkeeper confessed to killing 11 of his guests in the 1800s. And in the early 1900s, hunters shot as many raptors as they could. As a result, Hawk Mountain has no shortage of ghosts. The mountain is now home to a raptor sanctuary and a trail network. Take the Lookout Trail from the visitor center and explore the Sunset Overlook and North Overlook spurs. Longer routes are also an option, including a connection to the Appalachian Trail. A small user fee is required.
Distance: 2 miles round trip
Info: Hawk Mountain Sanctuary
Antietam National Battlefield
Antietam was the bloodiest battle in American history, with 23,000 casualties in a day. It’s no wonder that spooked visitors have reported hearing cannons and drums, smelling gunpowder, and seeing ghosts. To reach some of the battlefield’s more remote areas, take the Three Farms Trail from the visitor center. Turn around at the Sherrick Farm Trail, and head down Bloody Lane—a name that needs no explanation—on your return trip.
Distance: 4.2 miles round trip
Info: National Park Service