Society Adventures: A Lantern-Lit Tour of Sleepy Hollow Cemetery

Sleepy Hollow Cemetery at night (all photographs by the author unless indicated)

On a recent summer night with the air heavy from recent rain and the growing heat, the New York Obscura Society took the train from Grand Central Station up along the Hudson River to Sleepy Hollow. It was nearing night when we arrived at Sleepy Hollow Cemetery, but gas lanterns were waiting for us to illuminate our way through the darkening burial ground.

An angel at night

The theme of the tour was “Murder and Mayhem,” and the ramble through the horrific and devious stories of some of the more sinister people buried among the around 90 acres of the 19th century cemetery did not disappoint. Sure, you could go to Sleepy Hollow Cemetery on a sunny afternoon and appreciate the grand Rockefeller mausoleum or pay tribute to Washington Irving at his burial plot, but this tour led by Jim Logan and Christina Orbán-La Salle with the cemetery was a really unsettling and fascinating glimpse into the darker stories of local history.

The Helmsley mausoleum

While the cemetery and the town of Sleepy Hollow may be best known as the territory of the Headless Horseman (he’s even on their street signs), these were real tales of horror. There were some of greed and corruption, like the counterfeiter Joshua Miner or the “Queen of Mean” Leona Helmsley who once said “We don’t pay taxes; only the little people pay taxes,” and then left $12 million to her dog. There was also a burial place of a dog named Darling Leo, whose owner paid for local kids to weep daily at the grave. The cocker spaniel’s grave so irked a man named John O’Keefe who owned a nearby plot that he dug up the canine in the night, and then fell off the nearby bridge and broke his leg.

Gathered around the gas lanterns

Then there were those murderous stories like that of an 1870 killing caused (it is speculated) by a card game that went poorly and culminated with a man shooting point blank his two dinner guests in the face with a shotgun before bludgeoning his wife to death with the end of the weapon. Yet most disturbing was the Strong family, all buried in 1919. Late in that year, the father, Mason R. Strong, inexplicably attacked his whole family in their sleep with an axe before killing himself with a razor. His two daughters survived, but the other two children and their dead parents, including the father, were all interred beneath a simple stone.

Starting the tour in daylight

This all makes it sound like a rather grim evening, but it was also just a beautiful walk through the winding paths of the lush cemetery where fireflies were flashing and the gas lanterns cast trails of light over the ornate memorials and statuary. Below are some more photographs from the tour:

A memorial to Madame Restell, “The Wickedest Woman in New York”

The receiving tomb, where bodies were kept while tombs were being constructed or while winter made the ground too hard for grave digging

Inside the marble-lined receiving tomb

One of the open crypts in the receiving tomb

Gate to a cemetery plot (photograph by M. Sweeney Lawless)

Statue of Jesus, with missing fingers

Angel in the dark (photograph by M. Sweeney Lawless)

Another ornate statue (photograph by M. Sweeney Lawless)

Angel at night (photograph by M. Sweeney Lawless)

A tombstone and a gas lantern

It was a wonderful evening out away from the city noise to absorb some haunting history. Thanks so much to everyone who attended, and thanks to Jim and Christina at Sleepy Hollow Cemetery for a wonderful tour! Sleepy Hollow Cemetery regularly has walking tours and other events, like talks and even nighttime photography workshops, so visit their website and definitely explore the historic cemetery to discover both its beauty and dense, and sometimes dark, history.

The Obscura Society is the real-world exploration arm of Atlas Obscura We seek out secret histories, unusual access, and opportunities for our community to explore strange and overlooked places hidden all around us. Join us on our next adventure!

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