October Trip to Sleepy Hollow

As we all slip into the cozy jacuzzi that is Autumn, we all need the perfect place to drink in the foliage, breathe in the pumpkin spice and steep in a cup of haunted history. ย Sleepy Hollow is in the top three greatest places to celebrate Halloween, right next to Salem, Mass and New Orleans.

October in Sleepy Hollow ~ TheDreamyIdealist
^^ Don’t you wish you could float up to that roof-line and step your way to the top? Mr. Irving described the cottage as a “little nookery somewhat in the Dutch style, quaint, but unpretending”. It was built in the 1830’s as an expansion of the original two-room stone farmhouse which was built in 1690. The “1656” date on the side is another example of Mr. Irving’s gift for fiction. ๐Ÿ˜‰


“In the bosom of one of those spacious coves which indent the eastern shore of the Hudson…lies a small market-town or rural port…which is more generally and properly known by the name of Tarrytown”, N.Y.ย  “It is here, adjacent to the sequestered glen…of Sleepy Hollow” where you will find the home of America’s beloved man of letters, Mr. Washington Irving.

Mr. Irving stitched the Headless Horseman, Ichabod Crane and the pastoral beauty of the Hudson River countryside into our American lore with his most famed story The Legend of Sleepy Hollow. We all giggled and gasped as Rip Van Winkle slept and slept and slept.ย  And children continue to learn all sorts of misinformation, in public schools, about Christopher Columbus thanks to Mr. Irving’s gift for truthiness while making-up the biography A History of the Life and Voyages of Christopher Columbus.ย  (go on then, google it)

A visit to the author’s idyllic riverside home is a soothing and peaceful experience, particularly in Autumn.ย  Guided tours are intentionally kept small, and afterward you have the freedom to explore the handsome grounds.

TIP: In October they have Sleepy Hollow artifacts on display and there are apples in the orchard. Get your tour tickets in advance.


October in Sleepy Hollow ~ TheDreamyIdealist
^^ The vines hugging the exterior are wisteria. Mr. Irving planted them himself and they continue to thrive. Can you imagine how stunning they must look in bloom?ย  The little tower was called “The Spanish Tower” and was added after his trip to Spain.

October in Sleepy Hollow ~ TheDreamyIdealist


The Blaze is the most spellbinding Halloween spectacle I’ve ever attended.ย  More than 7,000 locally-grown, hand-carved, jack-o-lanterns haunt Van Cortlandt Manor (just North of Sleepy Hollow) each year.ย  Each area along the trail has its own theme, synchronized music and sound effects to set the mood as the lights inside the pumpkins flicker and fade in-and-out.ย  Some displays even move.

TIP: Buy your tickets in advance.ย  Tens of thousands of visitors attend each year, so tickets go very fast and you don’t want to miss out.


October in Sleepy Hollow ~ TheDreamyIdealist

October in Sleepy Hollow ~ TheDreamyIdealist

October in Sleepy Hollow ~ TheDreamyIdealist

October in Sleepy Hollow ~ TheDreamyIdealist

October in Sleepy Hollow ~ TheDreamyIdealist
^^ Inside of the covered bridge is a pumpkin planetarium complete with shooting stars and constellations.


A unique living history museum focused on the experience of enslaved people during the Colonial period.ย  Thankfully they do not sugarcoat slavery here. There are no euphemisms or downplaying of the suffering of the highly skilled laborers exploited and brutally condemned to a hellish life of mistreatment.ย  Guides go to great lengths to tell the individuals stories, use their names and talk about their relationships with compassion and dignity.

TIP: Buy your tickets in advance, especially in October when tours are limited.ย  This is the location used for the horror attraction Horseman’s Hollow, so if you go for a tour during the day and you’ll get to peak at the decorations without the scare.ย  Also, this is the location of the best gift shop in Sleepy Hollow, as it also serves as the admission location for Kykuit (the Rockefeller Estate).


October in Sleepy Hollow ~ TheDreamyIdealist
^^ So picturesque but such a terrible history.
October in Sleepy Hollow ~ TheDreamyIdealist
^^ The house was not a traditional home, as it was simply an occasional residence for the mill’s owner and housed the kitchen where the enslaved people cooked, worked and ate.
October in Sleepy Hollow ~ TheDreamyIdealist
^^ Decorations for Horseman’s Hollow. The little sign in front of the building says “Ichabod’s School House”. I wonder what scariness happens in there?!
October in Sleepy Hollow ~ TheDreamyIdealist
^^ The best gift shop in the area. Items align with the variety of tourism draw and are of higher quality than some of the other spots.


October in Sleepy Hollow ~ TheDreamyIdealist
^^ The Old Dutch Church is surrounded by a small cemetery known as the Old Dutch Burying Ground, which is where the Headless Horseman was buried and must return before day break after his nightly search for a head.

It is such a privilege to spend time in a building that is over 300 years old.ย  The quaintness of a stone structure with its charming windows and views only enhances the experience.ย  This building, like the other locations listed in this post are lovingly preserved with historic integrity.

October in Sleepy Hollow ~ TheDreamyIdealist
^^ The pulpit was clearly built by a master craftsman. The interior is simple and lovely. There is no electricity.ย  The candle light and wood-burning fire adds to the cozy factor.


October in Sleepy Hollow ~ TheDreamyIdealist

By far the best part of visiting the Old Dutch Church is the opportunity to see the legendary Jonathan Kruk reinact The Legend of Sleepy Hollow as Irving’s Legend.ย  I’m not one for live performances.ย  I like my comfy couch, camera angles and a pause button, but Mr. Kruk’s absorbing performance is masterful and fascinating.ย  Prepare to be engrossed on the edge of your pew as the story you think you know comes to life in this enchanting space.ย  Live organ music accompanies this compelling and unforgettable theatrical experience.ย  Even after reading all of the hype online, I was not prepared for what a truly remarkable event this is.

TIP: Get your tickets as early as possible.ย  There are limited performances and no trip to Sleepy Hollow in October would be complete without attending.ย  Also, in December Mr. Kruk performs Dicken’s Christmas Carol.



October in Sleepy Hollow ~ TheDreamyIdealist

The Sleepy Hollow Cemetery is behind the Old Dutch Church and Old Dutch Burying Grounds.ย  They offer multiple tour options during the day and evening.ย  The Classic Lantern Tour is at night and, as you may have guessed, everyone gets a lantern to carry, which adds atmosphere and much needed light, as the cemetery is incredibly dark.

Tour guides are professional and enthusiastic about the historical information they are sharing.ย  They are employed directly by the cemetery so there is no fear that you will be paying to hear inaccurate information or feel silly following around a costumed guide.

TIP: Wear sneakers and be prepared to have hurty feet by the end.ย  You’re walking and standing the whole time while going up and down hills.



Feel like recreating the journey of Ichabod Crane and Gunpowder on that fateful night?ย  Then start at the entrance to Patriots Park on US Route 9 (the main street through Tarrytown and Sleepy Hollow) next to the Andre Captured monument, which is on the border of Tarrytown and Sleepy Hollow.ย  Head into Sleepy Hollow on US Route 9 (you can walk or drive…it’s less than a mile one way).ย  Don’t stop until you’ve hit the Old Dutch Church perched up on the hill.ย  Below are some of the many Instagram-worthy things you’ll see along the way.

October in Sleepy Hollow ~ TheDreamyIdealist
^^ The original site of the Headless Horseman Bridge, directly before the Old Dutch Church, as described by Washington Irving in The Legend of Sleepy Hollow. Ichabod and Gunpowder were running for a covered wooden bridge but this one is quite nice as well. (TIP: If you’d like to get this particular shot, you’ll need to snap it quickly on your tour of Philipsburg Manor.)
October in Sleepy Hollow ~ TheDreamyIdealist
^^ Both Tarrytown and Sleepy Hollow are very proud of their heritage and connection to Mr. Irving’s legendary story.
October in Sleepy Hollow ~ TheDreamyIdealist
^^ The Headless Horseman Statue is tucked into a median in the road just before Philipsburg Manor. Finding parking near the statue is nearly impossible, so if you’re planning to visit the manor, you may want to walk up from there. (TIP: Sadly, several businesses around town display threatening signs in their parking areas on how quickly they will have you towed. As wonderful as it is to visit Tarrytown and Sleepy Hollow, I must admit they haven’t quite figured out how to manage the traffic influx and, in my experience, hospitality doesn’t extend far beyond the attractions.)


I know that for every attraction, I said “buy your tickets in advance”.ย  Please do heed this warning as most of these attractions sell out by the second week of October.ย  If you’re worried about cost, Historic Hudson Valley members get free, or discounted, tickets to most of these attractions, so joining is a great loophole for reducing your costs.ย  Seriously, do the math.ย  If you plan to attend multiple events, your membership pays for itself quickly and will reduce your over all cost by a significant amount.ย  There are additional perks as well.

Lodging on the Sleepy Hollow/Tarrytown side of the Hudson River costs a bit more, but crossing the river is a pain.ย  There’s loads of traffic on the Tappan Zee bridge, a $5 fee and it consumes far more time than you think it will.ย  If you’ve been sightseeing all day and want to go back to your hotel for a few hours before it’s time to go to the Blaze or the Cemetery Lantern Tour, you’re going to lose a solid 30+ minutes just screwing around with the bridge.

Eating vegan in Sleepy Hollow/Tarrytown is not as easy as it should be.ย  I hit up the Tarrytown Food Market on Route 9 and ate at a lot of diners.ย  Tarrytown’s main street is home to Sweetgrass Grill which has vegan fare, but they have odd hours so be sure to plan ahead.

Question of the Day:

What’s your favorite Halloween town?

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(cover image is in the public domain –ย The Headless Horseman Pursuing Ichabod Crane by John Quidor 1858)

2 thoughts

  1. I live on an island off the coast so it basically only ever feels like summer here. Your photos made me wish I could live in a permanent Halloween season in Sleepy Hollow! Definitely adding it to my travel to-do list!



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