• Dustin C. Kinard

Sleepy Hollow: Travel Tuesday 7


The Horseman comes, and tonight he comes for you!

It's Autumn, and the month of October. The leaves are falling, the weather is cooler, and a ghoulish fog sweeps the minds of children and adults, alike. Halloween is at our toes, and we spend the season celebrating the pumpkin spice and scary ghosts. Halloween costume pop-up stores litter the streets with their witches in the windows, ready to deck us out for holiday parties and trick-or-treating. It's the month that we search for the frights of the night in haunted houses and binge-watch scary movies.

This year, I decided to take a trip up, only a little north of my home in New York City, to a smaller and rural part of New York, known as Sleepy Hollow. I can remember sitting in third grade and learning all about Washington Irving's haunting tale of the small town. Learning of names like Ichabod Crane and The Headless Horseman. Cutting out orange construction paper pumpkin heads and glueing them on the shoulder of a headless torso I had colored with black crayon. To be honest, my little third grade self never thought the day would come where I would explore the streets of the tale's hometown.

A weekend in Sleepy Hollow, especially in the month of October, is really a wonderful experience. There are plenty of events happening and a lot of beautiful scenery with the leaves changing as well. My getaway weekend to Sleepy Hollow was packed- so much so that I didn't even get to fit in everything I had hoped. If you're looking for a chance to explore history, both literal and literary, and have a few spooks along the way, I would recommend traveling up for a weekend to this quiet little town in the Hudson River Valley.

The Great Jack O'Lantern Blaze at Van Cortlandt Manor brings people from ALL over. It is a number one attraction and you need to book your tickets in advance! This yearly sold out walk winds you along the path of thousands of illuminated pumpkins- all carved in crafty splendor. Pumpkins are put together and carved out, lit up at night to display some creative and iconic statues, landmarks, and designs; from the statue of liberty to the headless horseman himself. Grab yourself some apple cider doughnuts for the trail. Don't miss it!

Next, one cannot possibly visit Sleepy Hollow around Halloween and not visit the Horseman's Hallow at Philipsburg Manor. This English manor, built in 1693, was once the home of Frederick Philipse I, who is know for pretty much building and developing the origins of the town of Sleepy Hollow and many of its historical landmarks. Horseman's Hollow takes you on a scary haunted house trail along the grounds of the manor, where you may run into the town's iconic headless horseman! (Also, just a friendly heads up, there may be a thing dressed in all black that follows you at an uncomfortable distance as you walk the winding and scary trail. Keep a look out.)

On saturday morning, get up early, grab some breakfast, and head over to the Farmer's Market where you can pick up some pumpkin cookies, fresh breads, and watch kids play in the hay as they stuff scarecrows for the town. Next, just a short walk away, is the Sleepy Hollow street fair, where artsy and local vendors line the street with fun and creative souvenirs. Main Street isn't far away either, and is a great place to explore more of the neighboring town, Tarrytown, while checking out the thrift shops, art galleries, and trinket stores. For lunch, grab a taco at Taco Project (you can thank me later).

On Sunday, take it easy and spend the day exploring the Old Dutch Church, its church yards, and the Sleepy Hollow graveyard. Here you can find the Sleepy Hollow Bridge, thought to be the bridge used by the Headless Horseman, himself. Also, among the graves in the graveyard lie the remains of Washington Irving, along with the Rockefeller family and Andrew Carnegie. The gothic style of the headstones and old mossoleums make for a beautiful stroll, coffee in hand. End your stay with an early dinner at Bridge View Tavern before you head home. You can keep it seasonal with a pumpkin beer or cider alongside your huge stack of ribs or bison burger.

At night, there is also a reading of Washington Irving's tale "The Legend of Sleepy Hollow" at the Old Dutch Church. This was one of those events I didn't quite have enough time for, and tickets were also sold out way in advance. Therefore, I can't recommend it, but if you do go- let me know how it is! Seems like quite the thrill.. and I heard that some characters from the tale tend to show up as well.

As you explore the beautiful, picturesque town and all of its creepy legends, be careful and stay safe...

The Horseman rides at night!


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