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Day 60: The Legend of Sleepy Hollow

Along the east bank of the Hudson river, lies a village known as Tarrytown, tucked away in the quiet glen of Sleepy Hollow. There are many strange tales around the sprawling colonial-era towns of Westchester County, but perhaps none more legendary than that of the headless horseman. As far as ghost stories are concerned, we consider ourselves to be a civilized society, a people who don't believe in nonsense. At least that's what I thought.

Welcome to this sixtieth day of cocktails, my thirsty readers. I thought perhaps today, we could take a departure from the typical flavors of the tropics, journeying back before a time of Beachcombers and Traders. I always enjoy a nice smokey, warming drink, especially when it comes with a ghost story.


Set in the year 1790, "The Legend of Sleepy Hollow" tells the tale of Ichabod Crane and a night he would never forget. Crane, the newly appointed schoolmaster, has recently moved to the quiet glen of Sleepy Hollow, and immediately notices a young woman by the name of Katrina Van Tassel. Baltus Van Tassel, Katrina's father, was the wealthiest man in town, and Crane, ever the opportunist, saw a marriage to Katrina as his golden meal-ticket. The one thing he hadn't counted on, was the interest of another suitor, Brom Bones.

Being the local hero, Bones tried to challenge Crane to all manner of physical competition to win Katrina's hand, but Crane was a very cunning adversary. While Bones was a large brute of a man, Crane was a slim and lanky intellectual. He knew he could never compete with Bones' strength, so he used his wit to outsmart him at every turn. Even with more brains at his disposal than sense, Ichabod couldn't seem to woo Katrina, try as he might.

One night, the Van Tassels host a lavish party at their home. The entire town attends, including Ichabod and Brom. Crane dances, drinks, and does his best to charm the Van Tassels, hoping to secure his future with the lovely Katrina. Knowing he's a superstitious man, Bones decides to beat him at his own game, filling Crane's head with all of the local ghost stories he can remember. No story sticks in his head more than that of the headless specter, said to ride through the nights, terrifying all who cross his path.

According to local legend, the headless horseman was once a Hessian soldier. Just fourteen years earlier, after the Battle of White Plains, long stretches of roads along the south point of the Bronx River were filled with bandits and marauders, waiting to rob and kill those who passed. The Continental Army had moved on, leaving travelers vulnerable to attacks. As the story goes, there was one rider in the night, who drove all of the others away, a Hessian soldier, who'd lost his head to cannonball fire. Some said he still lurked along that same stretch of road.

Heavy-hearted and crestfallen, Ichabod leaves the party, and departs for home, having failed in his attempt to win the heart of Katrina. While traveling home, he rides along the very same road said to be occupied by the headless Hessian. With the tales of the supernatural still fresh in his dizzy head, he rides on, trying to convince himself there's no such thing as ghosts.

As he approaches the legendary bridge, said to be the one place where the headless horseman couldn't cross, he sees a unsettling figure on the road ahead. Sitting atop a large horse, the figure is tall, draped in a black cloak, and missing a very vital part of his anatomy, his head. Now, forgetting all sense of reason, Ichabod rides forward, hoping to reach the bridge, before this dark specter can close in on him. He rides on, looking behind him to see the headless rider raising a pumpkin in his hand, as if it were his own head. The rider hurls the pumpkin at Crane, knocking him off his horse, causing him to tumble to the ground.

The next morning, Crane is nowhere to be found. No remnants of the terrifying encounter can be found, except for a single smashed pumpkin. Many of the townsfolk just assume Ichabod had left town, after being embarrassed at the party by Brom Bones, but as for the truth of the story, and the identity of the mysterious rider, nobody truly knows.


The Legend of

Sleepy Hollow

1.5oz Apple Brandy (I prefer the Laird's Old 7 1/2, if you can find some)

.5oz Islay Scotch (I used Laphroaig 10 year)

Cocktail Coupe

On a wooden plank, or heat-proof surface, lightly torch apple wood chips.

Cover the smoking chips with an overturned cocktail coupe and set aside.

Stir and strain into the prepared coupe.

Flame an orange disk over the drink.

Carve the disk into a jack o'lantern design and garnish.


There comes that time in most of our lives, usually during childhood, when we cast off childish thing and stop believing in ghost stories. This world of make-believe usually passes out of our reality the same with Santa Claus, the Easter Bunny, and conspiracy theories. That's right, I see all you "truth seekers" out there. Keep on doing what you do, because it's really entertaining to the rest of us. Be safe out there everyone, wear a damn mask, and keep shaking.


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