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!

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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.

Amber R.
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!
Miranda | Spooky Little Halloween
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!
Chelsea Celaya
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!
Miranda | Spooky Little Halloween
Wouldn’t that pumpkin blaze be amazing to see? That’s like, my DREAM, for Halloween if/when I ever own a home!
Deigh
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…
Miranda | Spooky Little Halloween
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!
Mr. and Mrs. Halloween
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!
Miranda | Spooky Little Halloween
Right? They get all the good fall weather up there! :)
Candace Jedrowicz
How exciting! I would so love to do this!
Miranda | Spooky Little Halloween
Me too – I might actually get a chance to drop by Sleepy Hollow in April. Fingers crossed!
Candace Jedrowicz
Great story! It makes me want to visit and revel in its Halloween glory!
Miranda | Spooky Little Halloween
Me too – it would be absolutely magical in October!
RobertM
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!
Miranda | Spooky Little Halloween
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.
RobertM
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!
Miranda | Spooky Little Halloween
Much cooler than mine: Golden Eagles.
Paula Fields
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.
Miranda | Spooky Little Halloween
I have! There is one up in Dallas too. Need to find time to visit in the next few years. It looks amazing in photos.