(Not So) Sleepy Hollow : Discover the legends and ghosts that haunt this village just an hour outside of NYC this Halloween!

The Village of Sleepy Hollow is located next to Tarrytown, New York and shares the breathtaking Rockefeller State Park Preserve and eastern stream of the Hudson River: ideal for an autumn visit! Endless trees with a beautiful range of colours extend along the old Dutch houses and neighbourhoods by the Hudson Valley - you’ll quickly want to extend your stay!

The Rockefeller State Park Preserve hosts over 1,700 acres of greenery and over 45 miles of carriage trails with sites such as the Spook Rock, Raven Rock, and Carl’s Mill. Typical fall activities include hiking (on trails such as the Spook Rock or Witch’s Spring), horseback riding, bird watching, carriage riding, and fishing! It is also an ideal place to seek inspiration, where many artists come to paint or write in the peace and quiet of nature. Finally, if you are making your visit during the winter, activities include snowshoe trails, sledding, or yet again cross country skiing. 

Now let’s talk about what you’re really here for: experiencing the haunted village of Sleepy Hollow and exploring its most renowned sites!

The Village of Sleepy Hollow has duly worked on maintaining a spooky atmosphere and its ancient Dutch architecture. You can visit real life story sites such as the Philipsburg Manor, the Old Dutch Church and Cemetery, the former Mott Tavern, Patriots Park, and Raven Rock. As for the world renowned Headless Horseman Bridge, the original site described in the book has since, unfortunately, collapsed, leaving merely a sign indicative of where this used to be for those still interested in visiting. However, you can visit some of the other bridges made in the effort of maintaining the spirit of this monumental site ideal to pose on!

Formerly an enslaved property owned by Dutch colonial descendants prior to 1664, the Philipsburg Manor used to produce butter and other agricultural goods. Its main feature: a wooden water mill restored in 2016 by the New York State Council and still running today! Key in the American Revolutionary War (1775-1783), this Manor is where the British General Sir Henry Clinton who took over its occupancy after the Dutch wrote the Philipsburg Proclamation, naming all Patriot-owned slaves free. Considered a Nation Historical Landmarks since 1961, the Manor is filled with its 17th and 18th century furniture, authentic wooden structures, original water mill, and a large farmland estate open to the public today.

This Manor participated in the eerie decor of the village of Sleepy Hollow and was without-a-doubt home to enslaved descendants or colonial ghosts along the short story’s lines.

Also featured in the Legend as part of the greater decor of spooky Sleepy Hollow, the Old Dutch Church and its bridge is supposedly where the Headless Horseman disappears in a flame of fire after he haunts his victims. Moreover, the Church burial yard is said to host the bodies of past soldiers from the American Revolutionary War and where their ghosts awaken to haunt the village before rushing back by sunrise.

Historically speaking, this church was founded in 1685 and is indeed the resting place of past local citizens and American soldiers who have most likely inspired various characters of the Legend. This building was also designed by Frederick Philipse, Lord and first owner of the Philipse Manor.

Infamous for the night Ichabod and Katrina shared a dance at her parent’s estate, the Van Tassel Farm was inspired by the brick tavern once owned by the Revolutionary Mott Family. Indeed, the author of the Legend, Washington Irving, was a regular visitor to this estate in Tarrytown that combined an old house and 165 acres of farmland. To this present day, the building has been rebuilt to accommodate a high school. However, there is still a Landmark sign noting the previous presence of the site of Mott Tavern located at 18 North Broadway, Tarrytown, NY 10591.

This landmark was a focal point in the Legend as it describes Ichabod’s fatal last moments before he is chased by the supposed Headless Horseman past the Old Dutch Church in the dead of the night, where he is believed to be last seen.

Located between Tarrytown and Sleepy Hollow, this park is where Ichabod first witnessed the Headless Horseman before he is chased. History states that it was where the local militia captured British spy John Andre. Indeed, the Legend says that this spot is said to be haunted by this spy’s ghost after he was hung at Tappan by the Hudson River - and where evil still lurks…

Located in the Rockefeller State Park Preserve, Raven Rock is where the most ghost sightings are said to take place. More specifically, the Legend’s town murmurs the ghost of a woman in white lurking around this rock, shrieking in the cold snow. 

Finally, there are added monuments worth seeing such as the 18-foot Headless Horseman Statue beautifully designed by a local artist, Linda Perlmutter, the Sleepy Hollow Cemetery for more spooky tours, and the Andre Captors’ 1780 Monument.

1. The Horsemen: Terror Lies in Chaos

Enter - if you dare! This horror-filled Haunted House experience hosted by New York’s very best Psycho Clan is New York Times-renowned for its success in spooking all those who enter their premises. Exclusively located in Sleepy Hollow during the months of October and November, this event is highly recommended to visitors. You can book tickets here.  

2. Old Dutch Church Fest

Enjoy a bratwurst and a beer served by volunteers at Sleepy Hollow’s day-long annual Old Dutch Church Fest hosted in October. Wander in and around the Church grounds and you may just stumble across the path of past ghosts or the Headless Horseman himself! For more information, you can visit this webpage. 

3. Sleepy Hollow Cemetery Tours

A crowd favourite: the Sleepy Hollow Cemetery Tour is the most popular activity offered by the village’s tourist office. There is a choice of two tours: a day tour or a night tour for that extra spooky effect! And amongst these two tours, you can either go for the one-hour tour that focuses mostly on Irving’s short story, or the two hour option that goes beyond, offering extra information on the historical architecture and art behind the cemetery itself. Finally, a recent addition to these tours is the Murder and Mayhem Edition that offers an even more terrifying experience - leaving everyone shaking in their boots! But I’ll let you discover why here. 

For more activities around the halloween season, have a look at their fun packed calendar here!

1. Sleepy Hollow Hotel, Tarrytown, NY

Looking for that perfect cabin-like autumn experience? Look no further as the Sleepy Hollow Hotel located in its neighbouring town, Tarrytown, offers the most appropriate setting for those Irving fans out there. Breathtaking high ceilings, barn-like wooden structure, and stoned walls with grand fireplaces perfect for storytelling, the hotel’s main entrance area is spacious and cosy. The rooms are rather simple yet very comfortable and large. Finally, enjoy perks such as the fantastic indoor pool area, outdoor yard lounging areas, and a beautiful dining room! So what do you say, let’s make your stay at Sleepy Hollow unforgettable!

2. Castle Hotel & Spa, Tarrytown, NY

Also located in Tarrytown, the Castle Hotel & Spa provides an excellent proximity to the Sleepy Hollow Village grounds. Even more extraordinary, this hotel is built in a Medieval castle-type structure, truly taking you back in time and living in what it used to be like! The indoor interior replicates this theme, offering grand rooms with red-velvet curtains, stoned walls, and wooden floorboards and furniture. Feel free to wander around its beautifully landscaped gardens and unique outdoor structures, such as a life sized chess game! Finally, relax around the pool or yet again go in for a spa massage before dining over the views of the Hudson River.