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Kayak Has Mapped Out the Ultimate Spooky U.S. Road Trip

The Philipsburg Manor House in Sleepy Hollow, N.Y. (Photo: Wikimedia Commons)

Driver beware, you’re in for a scare… because the folks over at Kayak have put together a truly terrifying cross-country road trip stretching from New England to the West Coast. From haunted inns to creepy cemeteries, and old state hospitals to abandoned amusement parks, the 7,500-mile trip truly checks off every spooky box a Halloween-loving traveler could dream up.

Things get started at the Old Stagecoach Inn in Waterbury, Vermont (1), a bed and breakfast opened in the early 1800s that’s now listed on the National Register of Historic Places. There have allegedly been a number of spooky happenings at the inn, with paranormal investigators pinpointing rooms two and eight as the hotbeds of haunted activity, according to Kayak.

One of the specific stories tells of three guests who arrived in the middle of the night after everyone, including the inn’s owner, had gone to bed. When the owner (who regularly checked in all guests) ran into the unfamiliar-looking group the next morning and asked who had registered them, they told him they’d been let in by a grey-haired woman in a long dress. He had no idea who they were talking about; some have speculated it may have been the ghost of the long-deceased former owner, Margaret Annette Henry.

Stops two through seven on the road trip keep things in New England, including one stop each in Maine, New Hampshire, Rhode Island, and Connecticut, and two stops in Massachusetts. From the Old Stagecoach Inn, the arrow points east to Fort Knox in Prospect, Maine (2), where visitors aplenty have reported paranormal activity, and then south to Pine Hill Cemetery in Hollis, New Hampshire (3), which is referred to locally as Blood Cemetery and is considered to be one of the most haunted graveyards in New England.

From there, stops in succession include: the city of Salem, Massachusetts (4), which is steeped in the infamous history of the Salem witch trials, as well as a particular ghost tour offered by Salem Historical Tours (5); the city of Cumberland, Rhode Island (6), which is home to a haunted stretch of road; and the city of Mystic, Connecticut (7), where you’ll find Seaside Shadows and its various ghostly tour offerings.

Referred to as Blood Cemetery thanks to resident ghost Abel Blood, Pine Hill Cemetery can be found in Hollis, N.H. (Photo: Flickr)

Following the New England leg of Kayak’s Ultimate Spooky U.S. Road Trip are two stops in Sleepy Hollow, New York (yes, that Sleepy Hollow), the first being the former site of the Headless Horseman Bridge (8) along the Pocantico River. Though the original bridge has long since rotted away, a replica now crosses the river, allowing you to pass very near the spot where Ichabod Crane had his fateful encounter in “The Legend of Sleep Hollow.”

Adjacent to the contemporary bridge you’ll find the Old Dutch Church and Burying Ground (9), where the inspirations for Mr. Crane and Katrina Van Tassell are said to be buried. And just up the way is the Sleepy Hollow Cemetery, where author Washington Irving’s gravesite awaits.

Things take an insane turn as we turn our attention toward stop number ten: the Eastern State Penitentiary (10) in Philadelphia. Open for weekend tours with safety protocols in place, this empty, crumbling ruin of a prison was once “home” to the likes of some fairly notorious lawbreakers, including Al Capone. Nowadays, it’s managed by a nonprofit which provides regular tours and an annual haunted attraction called Terror Behind the Walls.

Once you’ve escaped the prison built with the goal of inspiring true regret in the hearts of inmates, it’s time for a stop in Baltimore at the gravesite of Edgar Allan Poe (11), followed by a hop, skip and jump over to Salubria Manor in Stevensburg, Virginia (12) — which is supposedly haunted by one Lady Spotswood, an original resident — and then a quick 250-mile jaunt to southern West Virginia and the remains of Lake Shawnee Amusement Park (13), which was literally left to rot in 1966 after some tragic accidents.

The next few stops include Chimney Rock State Park (14) in North Carolina; Bulldog Tours (15) in Charleston, South Carolina; Madison Square (16) in Savannah, Georgia; the St. Augustine Lighthouse (17) in Florida; and Sloss Furnaces National Historic Landmark (18) in Birmingham, Alabama — but the one in this southern swing that I’m really excited to tell you about is Bell Witch Cave (19) in Adams, Tennessee.

One of the numerous rusting attractions at the abandoned Lake Shawnee Amusement Park near Kegley, W.V. (Photo: Flickr)

If you’re familiar with the The Blair Witch Project (1999), the documentary-style horror movie filmed in the first-person, or any of its quasi-sequels (I’d recommend 2016’s Blair Witch), then this is one stop along the Ultimate Spooky U.S. Road Trip you will not want to miss. That’s because Bell Witch Cave served as the inspiration for the legend of the Blair Witch, although it’s also entangled with the tale of its namesake witch.

The *Blair Witch is creepy enough, but the *Bell Witch is said to be the spirit of a woman named Kate Batts, who swore on her deathbed that she would haunt John Bell, a local farmer, and his descendants for all eternity, believing Bell had cheated her on a land deal. For decades, people have traveled from all over to the rural town of Adams to visit Bell’s former farm and the nearby cave associated with the witch.

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The remainder of Kayak’s Ultimate Spooky U.S. Road Trip takes travelers through Mississippi, Louisiana, Texas, Oklahoma, Kansas, Colorado, New Mexico, Arizona, Nevada, and, eventually, all the way to California, where the Winchester Mystery House awaits in San Jose. To see all 29 (!) stops on the trip, just head over to kayak.com.

-LTH