An October Guide to Sleepy Hollow…

Sleepy Hollow, N.Y is fast-moving its way into the Halloweentown spotlight with a growing number of haunting events all October long! While this literary and legendary village has a number of events all year and Fall-long, this list is an easy access focus of all the October highlights and must-sees of the best month of the year!

As we make our way into the enchanting season that is Autumn, please keep in mind tickets for these events SELL OUT QUICKLY so if you see one you would like to attend, mark your calendars for ticket release dates!! DO NOT WAIT!

Many of the events are by TIMED TICKET ONLY and must be purchased in advance. Never show up without a ticket expecting to buy one there! Please check the events website listed for more info.

  1. The Horseman’s Hollow
  2. The Great Jack O’ Lantern Blaze
  3. Irving’s Legend
  4. The Legend of Sleepy Hollow — The Musical
  5. The Halloween Parade
  6. Halloween Block Parties!
  7. Sleepy Hollow International Film Festival
  8. The Sleepy Hollow Experience
  9. Cemetery Tours and Events
  10. The Haunted Hayride
  11. The Unsilent Picture
  12. Jay Ghoul’s House of Curiosities
  13. Lyndhurst Tours with Autumnal Decor
  14. Ghost Tours of The Music Hall
  15. A Step Back in Time
  16. Old Dutch Church Fest 

Historic Sleepy Hollow Must-sees…see bottom of page. 

  1. The Old Dutch Church and Burying Ground…including the gravesites of…
  2.      ~ Washington Irving
  3.      ~ Katrina Van Tassel 
  4.     ~ Brom Bones 
  5.     ~ Mother Hulda (New to Sleepy Hollow August 15th, 2019)
  6. The Headless Horseman’s Bridge
  7. Ichabod’s Route Fleeing From The Headless Horseman!
  8. The Captors Monument 
  9. Sunnyside
  10. Spook Rock and Hulda’s Hut

 

1 .The Horseman’s Hollow

“Philipsburg Manor transforms into a terrifying landscape ruled by the undead, the evil, and the insane.” – Historic Hudson Valley

A sprawling 18th-century farm and Colonial-era estate is transformed into Sleepy Hollow’s premiere haunted attraction throughout the chilling Octobers Eves! Revolutionary War soldiers, the minions of Ichabod’s Schoolhouse and of course, The Headless Horseman run wild through the Old Mill waiting to terrify you!

Tickets and info: https://hudsonvalley.org/events/horsemans-hollow/

Picture by Historic Hudson Valley

2. The Great Jack O’Lantern Blaze

“Meander through an 18th-century landscape and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on-site by our team of artisans!”- Historic Hudson Valley

Year after year, The Blaze does not disappoint Halloween lovers who come from all over the states to see this breathtaking display of the October spirit personified in the glowing brilliance of everything PUMPKIN!

Tickets and info: https://hudsonvalley.org/events/blaze/

3. Irving’s Legend

“Master storytellers offer dramatic performances of Washington Irving’s classic tale, featuring the Headless Horseman, Ichabod Crane, Brom Bones, and Katrina Van Tassel. Flavored with live spooky music, the spellbinding storytelling captivates all audiences.” –Historic Hudson Valley

Don’t miss an opportunity to hear The Legend of Sleepy Hollow from the Hollow’s best storyteller Jonathan Kruk in The Old Dutch Church which dating from 1697 is none other than the literary resting place of the Headless Horseman himself!

Tickets and info: https://hudsonvalley.org/events/irvings-legend/

http://visitsleepyhollow.com/things-to-do/old-dutch-church-tours-and-events/

4. The Legend of Sleepy Hollow- The Musical

“Set against the backdrop of Colonial America, William Allen Jones’ THE LEGEND OF SLEEPY HOLLOW infuses new life into the classic tale of Ichabod Crane and The Headless Horseman with memorable rock and pop songs and unforgettable ballads”

…The musical premiered October 2018 to “much fanfare at the Historic Mishler Theatre in Central Pennsylvania. The result was sold-out houses, artistic acclaim, and rousing applause.” – The Legend of Sleepy Hollow- The Musical

This year, The Musical is coming to town! Join Ichabod, Katrina and Brom this October and experience the Legend at the Irvington Tall Hall Theater. Tickets are on sale NOW!

For info: https://www.sleepyhollowmusical.net

For tickets:  http://www.irvingtontheater.com/theatre or 914-591-660

5. The Halloween Parade

Floats, dancing skeletons, and the Halloween Spirit come together in this wonderful community event year after year! So join us for the 18th annual Village of Tarrytown 2019 Halloween Parade! This year the parade will be held on October 26th at 5:30 and kicks off at Patriot’s Park. Tickets are not required and Costumes are highly encouraged!

A fundraiser will be held for the parade this year on September 26th at 5:30 at The Set Back Inn located at 33 Main Street, Tarrytown. Admission at the door is $25 and includes food and one complimentary drink. Come in costume!!!

For More Info: https://www.tarrytownhalloweenparade.com/

https://www.youtube.com/watch?v=VvIZB_Zx8B0

6. Halloween Block Parties!

Every year Tarrytown and Sleepy Hollow pull out all the stops to throw Westchester’s best Halloween block parties! Spread throughout the season, they can usually be found after events such as the Tarrytown Halloween Parade, or during events such as The Haunted Hayride! so check in with these events to see when the block parties will occur! They will be listed here http://visitsleepyhollow.com/calendar/

https://patch.com/new-york/tarrytown/tarrytown-halloween-parade-the-march

7. Sleepy Hollow International Film Festival

If it has not always been a dream to see Disney’s animated Legend of Sleepy Hollow in the very place it was born, are you even doing October right???

“Sleepy Hollow International Film Festival (SHIFF) celebrates this legacy of artistic inspiration and achievement. In addition to the bicentennial of his story—and an uncanny happenstance worthy of Irving himself—2019 is also the 70th anniversary of the beloved 1949 Walt Disney animated classic The Legend of Sleepy Hollow, and the 20th anniversary of Tim Burton’s acclaimed 2009 feature film, Sleepy Hollow. The festival will commemorate both of these big-screen landmarks with one-of-a-kind event showings, complemented by special guest appearances and panel discussions”. –Sleepy Hollow International Film Fest

For Tickets and info: http://sleepyhollowfilmfest.com/home/

8. The Sleepy Hollow Experience

An outdoor immersive theatrical performance at Washington Irving’s Sunnyside

“After seven years of sold-out performances around the country, Brian Clowdus brings The Sleepy Hollow Experience to the home of the Legend with an immersive evening production of Irving’s most famous ghost story. Meet Ichabod Crane and Katrina Van Tassel, along with a certain headless Hessian, in the very place where the author imagined them. Follow the characters from scene to scene with live music and a little bit of mayhem. Sip seasonal drinks and enjoy tasty treats at the Van Tassel’s harvest party. In a thrilling finale, see if you find out what really happens to Ichabod on the Sleepy Hollow Bridge.” – Historic Hudson Valley

Tickets and Info: https://hudsonvalley.org/events/sleepy-hollow-experience/

http://hauntedmountain.org/

9. Sleepy Hollow Cemetery Tours and Events

October in Sleepy Hollow would not be complete without partaking in one of the many haunting and thrilling events held within the iron gates of this iconic and sacred land. Night-time lantern tours, day-time walking tours, cocktails, storytelling, ghost stories, Poe, Irving and more all come “alive” in the month of October, so do not miss a chance to walk these hallowed grounds and come face to face with the real history of Sleepy Hollow.

For more info: http://visitsleepyhollow.com/things-to-do/sleepy-hollow-cemetery-tours/

http://sleepyhollowcemetery.org/

10. The Haunted Hayride

“Climb aboard Sleepy Hollow’s annual Haunted Hayride and hold on to your head! All seems well when you board your hay wagon in the brightly lit streets of downtown Sleepy Hollow. Rumbling off into the dark you realize too late you are heading down the Albany Post Road past the Old Dutch Church, following exactly Ichabod Crane’s flight from the Headless Horseman. Then you’re through a set of iron gates and the wagon slips into the dark woods of the hollow. Clattering across a wooden bridge, you start to hear shrieks and the sound of hoofbeats . .  “

Visit Sleepy Hollow

For more info: http://visitsleepyhollow.com/things-to-do/haunted-hayride/

http://visitsleepyhollow.com/things-to-do/haunted-hayride/

11. The Unsilent Picture

“Settle into an eerie evening performance featuring an original silent film starring Bill Irwin accompanied by live musicians and an in-the-flesh special effects Foley artist. Inspired by Washington Irving’s spooky tale “The Adventure of the Mysterious Picture,” the film was shot on location in the historic buildings of nearby Van Cortlandt Manor. Steeped in dark and moody turn-of-the-19th-century atmosphere, The Unsilent Picture unbends reality in the true spirit of Sleepy Hollow” -Historic Hudson Valley

For more Info: https://hudsonvalley.org/events/the-unsilent-picture/

https://www.imdb.com/title/tt9075054/

12. Jay Ghoul’s House of Curiosities

“It’s 1922, and a group of archeologists has unearthed an Ancient Egyptian tomb – but they barely have time to celebrate their discovery before the diggers each start dropping dead! Your group has arrived at the dig site (Lyndhurst mansion) to help determine the cause of the deaths – is it the Pharaoh’s curse or a cold-blooded killer?

You must solve the mystery before tragedy strikes again! Take a journey through the mansion to meet the cast of zany archeologists, local personalities, and unscrupulous smugglers. But be careful…each of them has their own secrets and superstitions.” -lyndhurst.org

For more info: http://lyndhurst.org/events/

http://lyndhurst.org/

13. Lyndhurst Tours with Autumnal Decor

“On the classic mansion tour in late September and throughout October, you will see the majestic vestibule and entrance hall, reception room, parlor, library, and the sumptuous Victorian dining room – all decorated with seasonal trimmings for the Autumn Season. The Open House weekends are a great opportunity for visitors to experience Lyndhurst filled with lavish autumnal decor and to walk through the house at their own pace without a guided tour.” -lyndhurst.org

For more info: http://lyndhurst.org/events/

lyndhurt.org

 

14. Ghost Tours of The Music Hall

Very new and exciting this year to The Old Tarrytown Music Hall…Ghost Tours! With all it’s many hauntings and legends, Tarrytown/Sleepy Hollow has yet to jump on the ghost band-wagon but here we have a trailblazer in the Music Hall which is an old and fantastic structure in itself and very active throughout the year as far as the community and spirits go! from their website…

Unexplained happenings and paranormal activity have been experienced at our 134-year-old historic theater.

Lights mysteriously turning back on after closing. The eerie sound of an unknown singer performing vocal scales in the wings after hours. High-profile artists refusing to stay in one particular dressing room because they “sensed a presence.”

Who or what could be the cause? Join us for a special “balcony to backstage” guided ghost tour to learn more about what we’ve discovered about the secrets of our theater, its intriguing history and the ghostly guests who still linger… if you dare!”

Click here for tickets and info: 

Ghost Tours of The Music Hall

1880s-Music-Hall-Exterior

Picture and info from https://tarrytownmusichall.org

15. Step Back in Time…

New This year to celebrate the Bicentennial of The Legend of Sleepy Hollow is a showing of the silent movie version of The Legend starring Will Rogers. Shown at The Old Dutch Church every Wednesday evening in October starting October 9th. 

More info to come on tickets and times…follow our Instagram page @Tarryhollowtown for updates…

Click here to see the black and white silent version preview 

 

16. The Old Dutch Church Fest

In addition to the Silent movie showing, The Old Dutch Church will also be hosting a festival every weekend in October in their burying ground! Hot Cider and Autumn treats as well as tours of the Church and burying ground take place throughout the month as well as appearances from The Headless Horseman himself are to be expected. 

For more information go to  www.rctodc.org

or call 914-631-4497.

odc

Ye Olde Dutch Church…

 

Historic Sleepy Hollow Must-sees!

Tickets are not required. Please be respectful of all Historic sites as they are not Halloween attractions, but an important part of our beloved history!

  1. The Old Dutch Church and Burying Ground…including the gravesites of…
  2.      ~ Washington Irving
  3.      ~ Katrina Van Tassel 
  4.     ~ Brom Bones 
  5.     ~ Mother Hulda (New to Sleepy Hollow August 15th, 2019)
  6. The Headless Horseman’s Bridge
  7. Ichabod’s Route Fleeing From The Headless Horseman!
  8. The Captors Monument 
  9. Sunnyside
  10. Spook Rock and Hulda’s Hut

 

1. The Old Dutch Church and Burying Ground 

Built-in 1685 and formally organized in 1697, The Old Dutch Church is the oldest extant church in New York and a historical landmark. The Church appears in “The Legend of Sleepy Hollow” as the resting place of The Headless Horseman. It is here that the Horsman lay, awakening at sunset and rushing back at daybreak, in-between riding to the American Revolutionary battlefields in search of his lost head which took it away with a cannonball! It is also here that Ichabod wooed Katrina amongst its tombstones and paths and served as the choirmaster. Notable Persons buried here include… 

Screenshot_20190821-152342_Instagram (1)

2. Washington Irving

Sleepy Hollow would not be on the map today without Mr. Irving penning “The Legend of Sleepy Hollow in 1820! Come visit the resting place of the man who started it all…

Irving is located in The Old Dutch Burying Ground on top of the Hill leading into Sleepy Hollow Cemetery. Follow the signs marked “Irving” to see his family plot. 

Screenshot_20190821-093118_Instagram

3. Katrina Van Tassel

The inspiration for Katrina comes from a woman named Eleanor Van Tassel Brush who lived in Tarrytown 1764 to 1861. Eleanor “Laney” was thought to have been very beautiful and bewitching. A story often told of her is that of the raid that descended upon her family during the Revolution. As the British soldiers tried to make off with household goods, one particularly crass officer tried to grab and make off with Laney for her striking features. The women of the household, being on their own with the menfolk away, took up any tools within reach and attacked the thug sending the men running off and leaving poor Eleanor alone! Irving used her beauty as inspiration but changed her name to Katrina…

katrina1

Photo From a great website, Josh Pincus is Crying. See this post to learn more! http://blog.marshotelonline.com/cemetery-visits/now-gather-round-while-i-elucidate/

 

4. Brom Bones

The rough and tough town blacksmith Abraham (Brom) Martling was known to be inspiration for the loved/hated character Brom Bones. After all, where would Ichabod be without a little friendly competition? 

bones

Photo From a great website, Josh Pincus is Crying. See this post to learn more! http://blog.marshotelonline.com/cemetery-visits/now-gather-round-while-i-elucidate/

5. Mother Hulda

August 15th, 2019 a remarkable thing happened in the Burying ground of The Old Dutch Church. A woman named Hulda who once known as “The Witch of Sleepy Hollow” was finally given a headstone after 200 years of being hidden away within its gates.

Hulda came to Sleepy Hollow in the 1770’s and lived in a little hut in the woods in what is now the Rockefeller Preserve. She was a healer, and as we all know women who were isolated healers in those days were naturally thought to be witches. The ministers of The Old Dutch Church told the townsfolk to shun her, which they did, but that did not stop Hulda from leaving baskets woven by hand filled with healing herbs on the doorsteps of the towns ill and ailing. Knowing it was her they would return the kindness with their own baskets of goods on her doorstep. She survived the woods this way along with trading with the Native Americans.

When the British came to Tarrytown, Hulda did not take to her hut and hide, but instead picked up her musket and powder horn and went swinging onto the battlefield. “Living up to her ancient name as a wood goddess” according to storyteller Jonathan Kruk, she not only broke the standoff but led the Redcoats away from the Tarrytowns.

Hulda was killed in battle, her broken body left in the woods. The soldiers took her back to her hut (located today at what is known as Spook Rock) and there they found amongst her things a bible and gold along with a will leaving the riches to the widows of Sleepy Hollow whose husbands were killed in war.
With this in mind she was taken to The Old Dutch Church, the very place which once shunned her, so she may be buried in hallowed ground with the condition that she not be given a gravestone….until today.

Mother Hulda’s hut is said to have been located in what is today The Rockefeller Preserve Park near Spook Rock (see below) and her grave is located on the northeast side of The Old Dutch Church in their burying ground. 

20190816_150830

6. The Headless Horseman’s Bridge

From http://www.visitsleepyhollow.com

“Unfortunately, the bridge where Ichabod Crane was unseated by a pumpkin is the most popular destination in Sleepy Hollow that doesn’t exist—at least, not in the form and location in which it appeared in Washington Irving’s short story The Legend of Sleepy Hollow. Whatever simple wooden span crossed the Pocantico River in the late 1700’s has long since rotted away. In fact, Sleepy Hollow village historian Henry Steiner has documented at least five distinct bridges that carried the Albany Post Road over the stream. Scarcely a trace remains of any except the most recent, the 4-lane concrete and steel U.S. Route 9 (the modern successor to the colonial-era Albany Post Road) bridge constructed by William Rockefeller in 1912 and reconfigured by New York State in the 1930s” -Jim Logan 

Today you can visit this modern bridge and take a picture next to the historic marker, which sits right before The Old Dutch Church. As stated on the website, the original structure is long gone, BUT if you walk up Gordon Ave. and keep left on Dell Street, you can peek across the stream and see a wall of stones embedded in the dirt and some believe those are all that is left of the real Headless Horseman Bridge! (see second picture and note the Old Dutch Church in the back left…The back of the Church use to be the front, so it would make sense that this bridge spanning the water lead to the front of the church) 

bridgeScreenshot_20190821-100200_InstagramScreenshot_20190821-100211_Instagram7. Ichabod’s Route Fleeing From The Headless Horseman!

Ready to have some fun? grab a pumpkin coffee and start at The Katrina Van Tassel farm (now the landmark condo complex) where Ichabod left the Halloween party the night he encountered The Horseman! 

Click on this link to see and follow the rest of the route of Ichabod that fateful night! I could not do a better job so here you go! 

Retracing Ichabod Crane’s Journey Through Sleepy Hollow

flee

8. The Captors Monument

Legend aside, what happened at the site of this monument changed the course of American History. We could have very easily been existing in British Territory had it not been for the quick thinking of three Patriots named John Paulding, David Williams, and Isacc Vanwart. The three militia stopped a man named Major John Andre, a British spy posing as a colonist who had just come from a meeting with Benedict Arnold who had just handed over to him the plans for West Point, a New York Strong-hold on the Hudson Valley. Had West Point been taken, the outcome of the Revolution might have been very different! Luckily for us, Andre was captured here and went on to be executed for his treason. 

andre

20190821_142519 (1).jpg

9. Sunnyside

(Tickets are required for an inside tour of the house but you are welcome to come see the outside of this beautiful home without one)

By far one of my favorite places in all the Hudson Valley is the former home of Washington Irving, called Sunnyside. A visit here in the Fall is exactly what is needed to step back in time and really appreciate what Irving has contributed to the world. Take a tour of his cottage, see his writing room and if you are lucky, his ghost! Irving and others are said to have remained at Sunnyside and after spending a day there you will see why they never wanted to leave! 

****This year only they are having The Sleepy Hollow Experience at Sunnyside!!!!****

See number 8 in the ticketed events section above! or visit https://hudsonvalley.org/events/sleepy-hollow-experience/

For daytime trips to Sunnyside visit….

Washington Irving’s Sunnyside

sunny

Picture from Hudsonvalley.org

10. Spook Rock and Hulda’s Hut 

‘Spook Rock was legendary from the earliest days of white settlement, a tradition which stretched into the folklore of the Native Americans. A large boulder sitting atop a hill, now graced with its own trail, Spook Rock Trail in Rockefeller Preserve, it was a gathering place for councils where leaders of the tribe would gather. Council rocks were chosen in part because they were believed to hold sacred powers, and Spook Rock was no exception.” Picture and info from https://www.gothichorrorstories.com/behind-urban-legends/hiking-rockefeller-state-park-preserve-looking-for-spook-rock-hulda-the-witch-and-the-non-headless-horseman-origins-of-the-legend-of-sleepy-hollow/

Nearby is the unknown location of Mother Hulda’s hut! (See #5 above)

Feeling brave and up for an adventure? this is the perfect Autumn hike! Click on the link above to learn more about this haunting location in the woods and the legend behind it! 

spook rock

 

Enjoy and Happy Hauntings!!!!!!!!!!