Halloween Hikes: The Spookiest Trails in America

There’s nothing like a scary story or creepy folklore to add some extra spirit to your hike. And there’s no better season than fall—the time for haunts and haints—to point your hiking boots in the direction of the spooky trails across the United States. The these hikes all feature some association with the supernatural (or, in one case, with a resident creature called a “cryptid”), from a little but mighty portentous black dog to a caterwauling spirit giving voice to her grief alongside one of the greatest canyons on the planet.

It’s worth noting, of course, that not all trails need have a local phantom or monster—nor some connection to a long-ago murder or massacre—to be spooky. Gnarled barren trees, dangling lichens or mosses, skeletal snags, otherworldly rock formations, the dark backwaters of a flooded wood, a clutter of strewn animal bones, simply a shift in light from friendly sunshine to dark overcast: Plenty of natural qualities can instill an eerie mood to a path.

(Sometimes it’s not even apparent what particular trigger, if any, makes a certain trail seem foreboding. No well-established paranormal reputation, no ugly bygone crime, no particularly strange-looking landscape or unknown noises: just a creepy or sinister feel. I have a hunch we humans have been having these inexplicable unnerving responses to certain places—these hunches, you might say—since about Day One.)

The following trails, though, have some pretty clear-cut credentials when it comes to the spooky and the strange, and as such they make a worthy Halloween bucket-list for any brave hiker.

Metacomet Trail: West Peak of the Hanging Hills, Connecticut

Part of the great traprock complex of the Metacomet Ridge in the Connecticut River Valley, the Hanging Hills form some of the highest ground along the East Coast south of Maine. Their apex, accessed by the long-distance Metacomet Trail (part of the New England National Scenic Trail), is 1,024-foot West Peak, which rises gently from the northeast while boasting sheer cliff-banded west and south faces.

Many hikers flock to adjacent East Peak to climb the 1900-built native-stone tower called Castle Craig. But the summit of West Peak presents such as expansive a view: all the way from the Berkshires to the iconic traprock height of Sleeping Giant to the south and Long Island Sound beyond. The impressive terrain comes complemented by an enduring paranormal legend: that of the Black Dog of the Hanging Hills. This refers to a phantasmal small black hound said to soundlessly haunt the traprock heights. It’s a sign of good fortune if seen once and a warning if it’s seen twice. But see it three times, the legend goes, and you’ve got a forthcoming date with the Grim Reaper.

The classic story of the Black Dog was related in an 1898 issue of the Connecticut Quarterly by the geologist W.H.C. Pynchon, who describes a wintertime visit to West Peak in the company of Herbert Marshall of the U.S. Geological Survey. Pynchon had already seen the Dog once in a rather friendly encounter; Marshall, meanwhile, had seen it twice, but laughed off the legend.

As the two reached the cliffs of West Peak’s southern rim, they spotted the Black Dog perched above them. “We saw his breath steaming from his jaws,” Pynchon wrote, “but no sound came through the biting air.” Spooked, Marshall told Pynchon, “I did not believe it before. I believe it now.” He then abruptly lost his footing and fell to his death in the ravine below.

As it happens, Pynchon himself met his end in the Hanging Hills some years after he penned his report—his body discovered in nearly the same spot where Marshall had come to rest. Pynchon’s demise, plus a number of other deaths in the vicinity (including a climber in 1972), have also been attributed by some to the silent canine specter.

So by all means hike the scenic spine of West Peak and enjoy those traprock vistas, but make sure you carefully tally how many times the Black Dog makes a cameo appearance. (Actually, we might recommend ditching the mountain after just the first glimpse—probably best to keep things on the lucky side of the fate spectrum, yeah?)

Bloody Lane Trail: Antietam National Battlefield, Maryland

September 17, 1862 was the bloodiest day of the blood-soaked American Civil War. The Battle of Antietam (or Sharpsburg) in Maryland saw nearly 23,000 killed, wounded, or missing, and many of those casualties resulted from the clash between two Union divisions and some 2,300 Confederate soldiers under General D.H. Hill, who’d holed up in an entrenched farm lane called the Sunken Road.

It took several hours for the bluecoats to overwhelm Hill’s men, and the carnage required to do so earned the Sunken Road a grisly new name. “Quite suddenly,” historian/novelist Shelby Foote wrote in his seminal The Civil War, “as if they had tumbled headlong by the hundreds out of the sky, dead men filled whole stretches of the road to overflowing.” Thus the Sunken Road became Bloody Lane.

Today you can walk this once-corpse-choked “holloway” on the 1.6-mile Bloody Lane Trail at the Antietam National Battlefield. It’s a solemn trek on which more than a few visitors have reported ghostly phenomena: the rattle of guns and marching drums, chanting and singing voices, the aroma of gunpowder. “Sometimes, people even report reenactments when none have happened,” writes Maren Horjus in Haunted Hikes.

As Rickie Longfellow notes in a Federal Highway Administration profile of Bloody Lane, an especially noteworthy observation was shared by a group of Baltimore schoolboys who claimed to hear singing of a melody like Deck the Halls while walking the trail. “The area was near the observation tower where the Irish Brigade charged the Confederates with a battle cry in Gaelic, which sounded like the Christmas carol,” Longfellow explains.

So keep those ears (and eyes) open as you tread Bloody Lane. Even if you don’t run across phantom soldiers, you’ll surely sense some sort of psychogeographic gloom hanging about the place, so convulsed with violence on that long-ago September day.

Sleepy Hollow Walkabout, New York

Washington Irving’s “The Legend of Sleepy Hollow” is one of the most enduring—and enduringly eerie—American ghost stories, and an autumnal visit to its setting is the perfect way to mark the Halloween season. Irving’s Headless Horseman may be a fictional specter, but it’s not difficult to conjure the distant clatter of undead hoofbeats while wandering the village of Sleepy Hollow on the east banks of the Hudson River.

The Horseman is (in Irving’s words) “said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannon-ball, in some nameless battle during the Revolutionary War, and who is ever and anon seen by the country folk hurrying along in the gloom of the night, as if on the wings of the wind.”

Tap into your inner Ichabod Crane on a dusk walk through the Sleepy Hollow Cemetery—where Irving is buried—and the adjacent churchyard of the Old Dutch Burying Ground, which figures in “The Legend.” Try to stay light on your feet while you do, just in case you have to dodge the spectral, decapitated rider’s hurled head.

Concho Billie Trail: Big Cypress National Monument, Florida

So that stinky, subtropical cousin of Bigfoot known as the Florida skunk ape almost assuredly doesn’t exist. But slog through the backcountry of Big Cypress National Preserve on the Concho Billie Trail (or, alternatively, the southernmost leg of the Florida National Scenic Trail nearby), and you might find yourself a temporary believer given the strangeness of the country. Savannas of slash pine and sabal palm, mucky cypress swamps, and strands spangled with airplants: This backland, home to legit flesh-and-blood phantoms such as Florida panthers and black bears as well as alligators and eastern diamondback rattlesnakes, looks and feels like the sort of real estate some bipedal, fetid, off-the-scientific-radar hominid might tromp around in.

Mammoth Cave, Kentucky

Kentucky’s labyrinthine Mammoth Cave isn’t only the longest-known cave system on the planet: It’s also said to be among the more haunted units of the National Park Service, generating better than 150 subterranean paranormal observations over the past couple hundred years. Hiking the shrouded limestone passages on a ranger-led tour, there’s no telling which of the sundry supernatural phenomena you might be privy to.

Periodically reported disembodied coughing from the shadows may link to an ill-fated underground sanatorium for tuberculosis patients housed in the depths of the cave back in the mid-19th century. Corpse Rock gets its cheerful name from the bodies of several sanatorium patients who succumbed and were laid out upon it.

Various specific Mammoth Cave specters have been identified, including the behatted ghost of Stephen Bishop, a slave who guided early visitors to the cavern system and also intrepidly mapped many of its features. The spirit of promoter Floyd Collins, meanwhile, who perished after being trapped by a cave-in in 1925, is thought to explain the man’s voice sometimes heard screaming for “Johnnie”—apparently Collins’ friend Johnnie Gerald, who according to Charles Wetzel in Haunted U.S.A. was the last man to speak to Collins during the drawn-out and ultimately unsuccessful rescue effort.

The Transept Trail: North Rim, Grand Canyon National Park, Arizona

This easy two-mile-long trail in the North Rim unit of Grand Canyon National Park edges a yawning, stair-stepped cleft called the Transept, a tributary of Bright Angel Canyon that itself empties into the main chasm of the Colorado River. The Transept Trail connects the vicinity of the North Rim Campground with the Grand Canyon Lodge, alternating between soaring views along the Transept brink and fragrant portals through the North Rim’s conifer stands.

All things considered, this must be among the most dramatically scenic of America’s haunted trails. The Transept Trail’s celebrity phantom is the Wailing Woman, a nighttime apparition sometimes considered the North Rim’s incarnation of a widespread figure of Mexican folklore, La Llorona. Various specific origin stories are given for the Transept Trail’s haunt: Some say she’s the ghost of a victim of a 1932 fire at the Lodge, known for door-slamming inside the building. Others suggest she’s the lingering spirit of a grief-wracked woman who committed suicide here in the 1920s after her husband and children fell to their deaths from the trail.

The Wailing Woman is typically described as wearing a white dress patterned with blue flowers, though your first notice of her will probably be her agonized cries on the rim-edge wind.

Written by Ethan Shaw for RootsRated and legally licensed through the Matcha publisher network. Please direct all licensing questions to legal@getmatcha.com.