#TravelTuesday: Sleepy Hollow, New York with Guest Ghoul Matthew Woods

?>

 

Welcome back to #TravelTuesday, a summer series on Spooky Little Halloween where we put a spooky twist on this popular hashtag and travel to haunted destinations across the globe.

This week I am very excited to welcome artist Matthew Woods to the blog with his breath-taking trip to Sleepy Hollow, NY. If you’re a Halloween lover on Instagram, you likely know Matt’s spooky pal Pumpkinhead who is always having amazing adventures and counting down to the best day of the year. You’ll see a Pumpkinhead original in this blog post (eek!). 

 


Sleepy Hollow, New York

By Matthew Woods, artist

 

“However wide-awake they may have been before they entered that sleepy region, they are sure, in a little time, to inhale the witching influence of the air and begin to grow imaginative, to dream dreams, and see apparitions.” – Washington Irving, The Legend of Sleepy Hollow

 

 

Whenever I come to a place full of legend and lore, I swear you can feel it. The air is different. My skin vibrates ever so slightly like when a stranger pays you a compliment or your first sip of coffee in the morning. That is the feeling you get when you enter Sleepy Hollow. A charming, historic little town that revels in its notoriety and invites a little darkness.

There is plenty to explore and see year round, but for the true experience, the time to go is October. In the autumn, Sleepy Hollow springs to life and bridges today with the past.

Home to and current resting place of Washington Irving, he is the one we have to thank for inviting the ghosts. The long-gone author sparked imagination and fear with his short story The Legend of Sleepy Hollow.

 

 

“The specter is known, at all the country firesides, by the name of the Headless Horseman of Sleepy Hollow.” – Washington Irving, The Legend of Sleepy Hollow

If you’re not familiar with the tale, I would highly recommend picking up a copy. If you’re more of a visual learner, my favorite interpretation is by Walt Disney and you can watch it here: The Legend of Sleepy Hollow, 1949. Though the ending is a little happier than the original story, it is certainly a charming version. Whether hunting the Headless Horseman or following in Ichabod Crane’s footsteps, there are a few things that you absolutely must do while visiting.

 

The Great Jack O’Lantern Blaze

 

 

One of the most breathtaking things I have seen. Take a slow stroll and a good camera because you’ll never again experience such unadulterated joy for the season. Alright, as an avid pumpkin lover I may be a little biased…

The Van Cortland Manor and grounds are covered with over 7,000 hand-carved jack o’lanterns. The ambient lighting, creepy soundtrack and stunning visuals will overload your Instagram with Halloween joy! Your creepling buddies will never have been more jealous.

 

Horseman’s Hollow

 

 

Who doesn’t love a period haunted house? Phillipsburg Manor is transformed into everything colonials feared about Sleepy Hollow. Goblins, witches, satanic cultists, OH MY! Not to ruin the big finish, but you just might learn a thing or two in a deranged Ichabod’s classroom before facing the headless legend himself!

 

Sleepy Hollow Cemetery Lantern Tour

 

 

Lit only by kerosene lanterns, this is the tamer nighttime event. Hear the history and sordid tales of New York’s most notorious residents. Murder, scandal and wickedry saturate these hallowed grounds. Make sure you leave a coin or stone on Washington Irving’s grave as a remembrance.

 

Bridge View Tavern

If you need a little liquid courage before braving haunted attractions, this local watering hole has everything you need. Overlooking the Hudson River, they have a full bar, a good tap line, plenty of comfort food and a beer garden.

 

Coffee Labs Roasters

For one of the best cups of coffee I can remember, visit Coffee Labs. They take their joe very seriously and you can taste it. Death before decaf!

 

 

 

Next stop: we wrap up our summer of haunted travel with a spooky location from me…right here in Texas!

Matthew Woods is the artist behind the daily adventures of Pumpkinhead. Thinly veiled, Pumpkinhead tells stories from Matthew’s life as they both wait for the most sacred of all days, a day where they are normal for once…Halloween! Born and raised in Massachusetts. Transplanted to New York City. Matthew is a self-proclaimed Renaissance Man practicing many different art forms in various mediums. Never without a sketchbook in hand, he draws most of his inspiration from nature, horror, rock ‘n’ roll and friends on a daily basis. Photo by Johannes Oberman.

Miranda | Spooky Little Halloween

Miranda is the Houston-based writer, blogger, and Halloween lover behind Spooky Little Halloween, the blog celebrating October 31st all year long. Her favorite Halloween things include pumpkin guts, chocolate bars in her trick-or-treat pail, real haunted houses (including the one she lives in!), and historic cemeteries.

18 Comments

  1. Reply

    Amber R.

    August 16, 2017

    What an awesome post!! I too, love visiting places with eerie history, legends, & folklore. Mikey and I are hoping we have the money and time to visit Sleepy Hollow this year. If it doesn’t work out, we’re going next year for sure!

    • Reply

      Miranda | Spooky Little Halloween

      August 18, 2017

      Very cool! I can’t wait to read your post after you go. You’ll have to let myself and Matt know if you visit any of these spots!

  2. Reply

    Chelsea Celaya

    August 18, 2017

    Love the image! So cute and appropriate~! I had no idea so many things happen in Sleepy Hollow! This place is definitely going on my bucket list. Especially to see those thousands of pumpkins! What an amazing place!

  3. Reply

    Deigh

    August 31, 2017

    I got to go last year. It was September, so it was a bit before the festivities began, but I thoroughly enjoyed the history and ambience, even without the seasonal organization. I was surprised by just how populous the area was. Even with its proximity to NYC, I still pictured SH as a rural (farming) area. It definitely is not. It’s charming, maybe quaint, but certainly busy and bustling. That is, until you enter the Dutch church cemetery…

    • Reply

      Miranda | Spooky Little Halloween

      August 31, 2017

      I’ve been up to Chappaqua twice in the last four years for work and haven’t taken the time to pop over to Sleepy Hollow. Such a shame since it is so close!

  4. Reply

    Mr. and Mrs. Halloween

    September 6, 2017

    Great post! So eager to experience an autumn/Halloween season in the North East! Beautiful colors and lots of history and lore to keep things spooky!

  5. Reply

    Candace Jedrowicz

    February 23, 2018

    How exciting! I would so love to do this!

  6. Reply

    Candace Jedrowicz

    March 26, 2018

    Great story! It makes me want to visit and revel in its Halloween glory!

  7. Reply

    RobertM

    January 25, 2021

    Love the article!

    I grew up in Sleepy Hollow. When I lived there it was known as North Tarrytown.

    We didn’t have the events that they have now, but it was still a very, very cool place to experience Halloween. One year a man held a seance in the Old Dutch Church cemetery and he asked some of us kids to go to Irving’s grave to check his birth date or date of death, something like that.

    The grave is deeper in the cemetery, nobody around and of course our imaginations ran away with us. Every little sound was a ghost! So funny.

    Good times!

    • Reply

      Miranda | Spooky Little Halloween

      January 26, 2021

      How magical! I had the BEST time wandering the town about a year after this was written by my friend Matt. It was such a beautiful little town.

  8. Reply

    RobertM

    January 27, 2021

    Miranda, it was a neat place to grow up in!

    And I still say that our high school, Sleepy Hollow High, has the coolest mascot EVER!

    Go Headless Horsemen!

  9. Reply

    Paula Fields

    June 28, 2021

    Have you heard of or seen The Jack o lantern trail in Louisville KY?
    Hubby and I went few years ago. Most amazing display I have ever seen. The Blaze in New York is on my bucket list.

LEAVE A COMMENT

This site uses Akismet to reduce spam. Learn how your comment data is processed.

RELATED POSTS