AWM Destinations: Sleepy Hollow

Welcome to AWM Destinations, the world’s leading travel agency for faraway and fantastical destinations. Each week, AWM Destinations will showcase a unique and exciting vacation destination and spotlight some of the exciting attractions, dining, and lodging options available at each location. We hope you enjoy this series of articles and look forward to hearing about your travels with AWM Destinations.

Written by Matthew Masino


Sleepy Hollow

As we begin the month of October, AWM Destinations is excited to highlight some of the spookiest destinations in the world. Today we’ll begin our journey in the town of Sleepy Hollow. Found just a little more than two miles away from the town of Greensburgh (more commonly known as Tarry Town), Sleepy Hollow is rich with haunted spots and local superstitions including the world famous Headless Horseman. The area is also said to be the preeminent destination for astrologers as shooting stars and meteors can be seen there more than anywhere in the country.

Historical Buildings

Sleepy Hollow
Visit Sleepy Hollow today!

Sleepy Hollow was founded in the mid-15th century by descendants of the original Dutch settlers and many of the structures they built are still around today for you to visit. Found at the foot of a woody hill, you can still hear the murmur of students combing through their textbooks in the one-room schoolhouse. Constructed primarily of logs, the schoolhouse is a fantastic destination for travelers interested in historical architecture with daily tours sponsored by the Sleepy Hollow Historical Society. During the tour, you’ll hear the tale of Ichabod Crane, the now infamous school teacher involved in the legend of the Headless Horseman.

Make sure to check out Town Square and visit some of the historic businesses including the Irving Tavern and the Old Dutch Church. Take advantage of the Sleepy Hollow Historical Society’s Haunted Tours and discover the tales of ghosts and goblins once shared on porches by old Dutch wives.

The Legend of the Headless Horseman

Painting of the Headless Horseman pursuing Ichabod Crane
Artist rendition of the Headless Horseman chasing Ichabod Crane

Perhaps one of the town’s most famous stories is that of the Headless Horseman. The story tells of a German soldier who fought on the side of the British during the Revolutionary War. Riding his horse into some unnamed battle, the soldier suddenly found his head being carried away by a cannonball. Allegedly, the soldier’s body was buried in the church graveyard and his ghost has been seen riding toward the site of the battle in a nightly quest for his missing head.

Many years later the schoolteacher, Ichabod Crane, who one fateful night was traveling home on his neighbor’s horse, Gunpowder, with the sky growing darker and the stars shrinking into the sky, found himself facing the Galloping Hessian (as many townsfolk were said to have done before). Believing he could find safety across the Church’s bridge, he rode his horse as fast as he could hoping to cross it. But it would not matter, for when he turned back the Headless Horseman removed the flaming pumpkin from atop his shoulders and threw it at the poor school teacher.

The next morning, upon the school teacher’s absence from class, they discovered only Ichabod’s hat and a shattered pumpkin lying on the ground near some hoof tracks deeply ingrained in the road. Despite an investigation, the body of Ichabod Crane was never found. Some say that Ichabod merely ran away out of fear of the Horseman and moved across the country to become a lawyer and start a family with some rich widow but the legend (and those who tell it) maintain that Ichabod was spirited away by supernatural means from his visit with the Headless Horseman. Perhaps on your visit you can uncover more about what really happed to Ichabod Crane.

Merry Making at the Van Tassel’s

photo of the headless horseman
Book your trip to Sleepy Hollow today, but keep your head on a swivel…

One of the fantastic benefits of travelling with AWM Destinations is our catalogue of exclusive events and destinations. During your visit to Sleepy Hollow, you’ll be treated to a period-accurate Autumnal Gathering held at the historic Van Tassel Manor. Put on your petticoats and breeches for this charming town festival with dancing, bobbing for apples, and the occasional spooky story. You’ll enjoy bountiful harvests of corn, cakes, and hasty-pudding. You’ll dance and sing the night away to a town elder playing classics of the era on his three string fiddle. Your night at the Van Tassel’s will be unforgettable, just make sure not to take the wrong way home or you may run into the Headless Horseman…

If you’re still looking for a vacation destination this fall, look no further than Sleepy Hollow, a town so rich in legend and superstition, you won’t know what to believe. When you book with AWM Destinations, you have the assurance of a world renowned travel agency behind you who can answer any question you may have. Click here to discover more about the rich history of Sleepy Hollow and book your trip. We hope to see you traveling with us soon.


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AWM Destinations is the world’s leading travel agency to faraway and fictional destinations. We provide custom travel services involving air, rail, twister transport, car rentals, magic portals, hotel reservations, tours, and sightseeing. Our mission is to connect travelers from around the world with a diverse range of destinations and experiences. From theme parks to tropical islands to fantasy kingdoms, AWM Destinations is your one-stop shop for inside access to the most exciting and exclusive destinations in the world, and beyond.

Matt is a Storyteller at the American Writers Museum in Chicago

Matthew Masino joined the team at the AWM in December 2019. He graduated from Columbia College Chicago with a BFA in Theatre Directing in May of 2019. While not working at the museum, Matthew is a theatre director and creator. He has worked with the International Voices Project, the Chicago Fringe Festival, and BYOT Productions on various projects. He is excited to share his love for the written word with all that visit the museum.

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