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Visit Sleepy Hollow History and happenings in Sleepy Hollow and Tarrytown, New York
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That time he took a side hustle at a dealer.
25/02/2025

That time he took a side hustle at a dealer.

Hudson River ice at Horan’s Landing. Pro tip: good views from the oyster bar at !
25/01/2025

Hudson River ice at Horan’s Landing. Pro tip: good views from the oyster bar at !

Today’s snow reminded us Tarrytown and Sleepy Hollow were very early adopters of bobsledding. Between the late 1870s and...
20/01/2025

Today’s snow reminded us Tarrytown and Sleepy Hollow were very early adopters of bobsledding. Between the late 1870s and about 1920 a day like today would have seen racing teams hurtle down Cortlandt, Vally, and Wildey Streets, the aptly named Cemetery Hill (Route 9 from the Civil War monument to the millpond), and Gould Hill (Route 9 from to today’s Montefiore).

The Laura T once belonged to Tarrytown constable Charlie Schneider who was known to give rides to kids down Paulding Avenue.

There were numerous local sled builders. Fred and Otto Bouck were notable as was Henry Godstrey. The greatest, however, was Leander Jacobs. Jacobs was an expert racer as well as builder. His appearance on a snow-slick hill would elicit wild cheers from crowds of spectators.

Jacobs’s house was at the corner of College Avenue and Valley Street where Esquina Latina market stands today. He and wife Mary are buried side by side in Sleepy Hollow Cemetery.

January 5, 1914.111 years ago today William Bailey, an employee of John D. Rockefeller, took inspiration from Washington...
05/01/2025

January 5, 1914.

111 years ago today William Bailey, an employee of John D. Rockefeller, took inspiration from Washington Irving’s “The Legend of Sleepy Hollow”. Saddling his horse in the small hours of the morning, costumed to obscure his head, he rode off through the village to wreak havoc among the hardworking residents out and about at that hour. (For historical perspective, before the advent of supermarkets and Costco, numerous local bakeries, dairies, produce dealers and butchers would have been out and about at that hour of a Monday morning.)

Bailey spent some time in Tarrytown Hospital, precursor of today’s

North Tarrytown’s Finest (today’s ) noticed and gave chase. As Bailey turned his steed onto Beekman Avenue, its shoes slipped on the brick roadbed and horse and rider went down.

Bailey suffered a dislocated hip and a badly lacerated head. History doesn’t record the fate of his steed.

records burial of a William Bailey a decade later but so far we can’t confirm it is one and the same. Perhaps when finishes scanning of historical newspapers we will know the rest of the story.

This morning published a short bio on Sleepy Hollow’s long-time headless horseman, Hugh Francis. At age 89, with two ne...
25/10/2024

This morning published a short bio on Sleepy Hollow’s long-time headless horseman, Hugh Francis. At age 89, with two nearly-new hips and a new knee, he is still in the saddle!

More witches in Headless Horseman country? Back in 1932 our neighbor to the north, tired of giving directions to Sleepy ...
10/10/2024

More witches in Headless Horseman country? Back in 1932 our neighbor to the north, tired of giving directions to Sleepy Hollow, offered its own legend to compete with Ichabod and the horseman.

The article above, which appeared in The Daily Item of Port Chester, New York, recounts the tale of an old mill formerly located in what is now downtown Ossining. Mysterious happenings at midnight in the busy season stopped the mill completely, and so after much fear and quivering the miller decided to slay the ghost.

Curious about what happened? Click the link in our bio and then “The Bewitched Mill of Sing Sing”!

Howl the night away at the first annual Haunted Kill event on Friday, October 18th! The Village of Ossining’s Sing Sing ...
10/10/2024

Howl the night away at the first annual Haunted Kill event on Friday, October 18th! The Village of Ossining’s Sing Sing Kill Greenway, located at the Joseph G. Caputo Community Center, transforms into a dark and foreboding Trail of Terror. For information and tickets to this this spine-tingling experience: Ossining Recreation and Parks Department, https://www.facebook.com/events/881235153517799/ or (914) 941-3189

⁠ Haunted Kill will feature bone-chilling monologues, each inspired by a unique historical figure or event, written and performed by members of Westchester Collaborative Theater. There will also be live music by the Sci-Flies as well as the Moon, Serpent and Bone Oddities and Curiosities Night Market. ⁠
⁠
The Haunted Kill is a community collaboration between the Village of Ossining, the Ossining Recreation and Parks Department, , and the Ossining Placemaking Committee.

Witches in Headless Horseman country? Why yes! “Billie” Burke, best known as the good witch Glinda in the 1939 film vers...
09/10/2024

Witches in Headless Horseman country? Why yes! “Billie” Burke, best known as the good witch Glinda in the 1939 film version of ‘The Wizard of Oz,’ lived just down the road.

Scarecrow’s Ball is an all-day, Oz-themed Halloween extravaganza with a dash of magic and a sprinkle of mischief. It’s got everything from “witchy” brews to a costume contest, perfect for those who think their scarecrow outfit is next-level fabulous. The day kicks off with a Drag Queen Story Hour followed by live music, old-school games, a raffle, and a chance to craft your own wand. Expect prizes, laughs, and more treats than tricks. It’s Halloween, but with glitter and sass!

Tickets just launched for The Legend of Sleepy Hollow: A Radio Play. This live performance of Irving’s classic tale take...
08/10/2024

Tickets just launched for The Legend of Sleepy Hollow: A Radio Play. This live performance of Irving’s classic tale takes place the weekend of October 25-27 at Scarborough Presbyterian Church. For more information and tickets, visit

Looking for a room with a boo for your stay in Sleepy Hollow? According to local lore, the spirit of Sybil Harris King c...
05/10/2024

Looking for a room with a boo for your stay in Sleepy Hollow? According to local lore, the spirit of Sybil Harris King continues to inhabit her long-time home where she can be heard pacing the second-floor hallway. The King mansion is now part of , a hotel and event venue. One TripAdvisor review says: “Get the room with the ghost. Room 293 is the room that someone haunts. We did not know this until the second day, when the maid asked where our monitoring equipment was. Had dreamt the night prior of a brunette woman trying to climb into bed with us and of children playing under the bed.”

If room 293 is already booked, you can reserve a seat at the hotel restaurant in the King mansion.
pays tribute to the cuisine of Hong Kong, with a focus on noodles, Cantonese barbecue, and dumplings. If you need assistance spotting the spirit of Sybil Harris King from your table, the house stocks three varieties of absinthe—la fée verte—“the green fairy” that brought visions to Vincent Van Gogh, Oscar Wilde, Charles Baudelaire, and countless artists and writers.

Sybil and her husband Frederick are buried nearby in where you can take a guided tour.

Want more about historic hauntings? Click link in bio and then “ghosts of Sleepy Hollow”. Happy hauntings!

Our friends at are in full swing with October decorations and Autumn cocktails. The Notes from Irving seasonal sip is g...
04/10/2024

Our friends at are in full swing with October decorations and Autumn cocktails. The Notes from Irving seasonal sip is garnished by none other than a note from Washington Irving himself! Game and Trivia nights are joined in October by two nights of Palm Readings. And of course The Tapp has front row seats to the on October 26!

Sleepy Hollow hoodie spotted in Madrid tonight.
03/10/2024

Sleepy Hollow hoodie spotted in Madrid tonight.

Welcome to spooky season in Sleepy Hollow! While the Headless Horseman gets all the press, there are actually a host of ...
02/10/2024

Welcome to spooky season in Sleepy Hollow! While the Headless Horseman gets all the press, there are actually a host of other ghosts in the area. One of the most infamous had the time of its afterlife in the villages of Piermont and Sparkill in March of 1887 until it met its demise near this stone bridge. For the full story, click the link in our bio and then “Piermont Ghost”.

is 5 miles from Sleepy Hollow as the raven flies, or 15 minutes by road, directly across the Hudson from . , the closest Bed and Breakfast to Sleepy Hollow, has a front seat to the haunted road.

Happy October! As the Village of Sleepy Hollow celebrates 150 years, and turns 175, there are more things than ever to ...
01/10/2024

Happy October! As the Village of Sleepy Hollow celebrates 150 years, and turns 175, there are more things than ever to do and see in the hollow. Click the link in bio for the complete calendar of events!

The ghouls are gathering outside J. P. Doyle’s. Must be time to turn the calendar to October!
01/10/2024

The ghouls are gathering outside J. P. Doyle’s. Must be time to turn the calendar to October!

Our neighbors to the south have thrown down the gauntlet: Rip van Winkle or the Headless Horseman. We think this is rigg...
26/09/2024

Our neighbors to the south have thrown down the gauntlet: Rip van Winkle or the Headless Horseman. We think this is rigged, since is hosting their October 18 party in the shadow of Irvington’s Rip van Winkle statue, but you decide!

Come in costume to a performance of Winkle vs.
Horseman by and stay for the Halloween Block Party featuring crafts, games, face painting, food, and a beer garden hosted by .dobbs!

WHEN: Fri, October 18, 2024
WHERE: Irvington’s Aqueduct parking lot (across street from the Main St School)

Grab your tickets for the 7:00 PM or 7:45 PM
performance of Winkle v. Horseman (30-minutes) from

🎃Check in for your performance at the Halloween Block Party at Irvington’s Aqueduct
Parking Lot starting at 6:30 PM.

🎃 A few minutes before the show, groups will be guided on a candlelight walk to Rivertowns Playhouse’s backyard theater.

🎃 After each performance, you will walk back to the block party to continue the fun!

🎃 Costume contests (kids and adults) will be won at the night’s end (around 8:30 PM)

Calling all sleuths! This year’s Nancy Drew Convention lands in Sleepy Hollow October 2-5. Each year the convention foll...
24/09/2024

Calling all sleuths! This year’s Nancy Drew Convention lands in Sleepy Hollow October 2-5. Each year the convention follows Nancy’s footsteps from one of the 56 novels published between 1930 and 1979. This year the theme is 1937’s The Haunted Bridge. Find more clues to this haunting weekend at

Hard to believe the is just 36 days away! Stop by Wednesday, September 25 at 5:30 pm for the annual parade fundraiser!...
20/09/2024

Hard to believe the is just 36 days away! Stop by Wednesday, September 25 at 5:30 pm for the annual parade fundraiser! Costumes welcome!

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