The Legend of Sleepy Hollow Fly-In | Hosted by VirtualBlue

The Legend of Sleepy Hollow

The story of the Headless Horseman has transcended time without a clear reference to the creation of the character.

The story is set in 1790 in the countryside around the Dutch settlement of Tarry Town (historical Tarrytown, New York, in a secluded glen known as Sleepy Hollow. Sleepy Hollow is renowned for its ghosts and the haunting atmosphere that pervades the imaginations of its inhabitants and visitors. Some residents say this town was bewitched during the early days of the Dutch settlement, while others claim that the mysterious atmo

After the Battle of White Plains in October 1776, the country south of the Bronx River was abandoned by the Continental Army and occupied by the British. The Americans were fortified north of Peekskill, leaving Westchester County, a 30-mile stretch of scorched and desolated no-man’s-land, vulnerable to outlaws, raiders, and vigilantes. Besides droves of Loyalist rangers and British light infantry, Hessian Jägers—renowned sharpshooters and horsemen—were among the raiders who often skirmished with Patriot militias.

The Headless Horseman, said to be a decapitated Hessian soldier, may have indeed been based loosely on the discovery of just such a Jäger’s headless corpse found in Sleepy Hollow after a violent skirmish, and later buried by the Van Tassel family, in an unmarked grave in the Old Dutch Burying Ground.

Local historians have presided that accounts of the Headless Horseman have been witnessed riding around the county of Westchester, as far East as White Plains where Westchester County Airport was built. The disturbance of the land has stirred up the spirits that once battled and lost their lives and can be seen at times roaming near HPN, including, the Headless Horseman.

Airport: Westchester County - KHPN

Date & Time: 2023-10-31T10:00:00Z

Server: Expert Server

Event Type: Fly In

KHPN is a regional airport so no heavies are allowed.

ICAO Airline Aircraft Aircraft Aircraft
KMIA JetBlue BCS3 E190 A320
KDTW JetBlue BCS3 E190 A320
KRSW JetBlue BCS3 E190 A320
KDCA JetBlue BCS3 E190 A320
KBNA JetBlue BCS3 E190 A320
KBOS JetBlue BCS3 E190 A320
TJSJ JetBlue A320 A321
CYTZ Porter Dash-8
KMDW JSX Challenger350

If you want to control any station at KHPN, please comment on this topic or PM me with the desired frequency(s)!

KHPN ATC - Controllers Needed

Frequency Controller
Ground -
Tower -
Approach -
Departure -
New York Center -

This event is being held on the Expert Server and conduct is expected to be professional. Please act accordingly to avoid any violations!


Commercial Parking available at Main Terminal.

Corporate Parking available at GA Parking






This Event is on the Expert Server. Act accordingly.


Please follow all ATC instructions.
If you have questions, please ask.
Be respectful during the event.
Be safe.
Have fun!!



The thumbnails and photos look epic, great work! Sadly I cant join at the moment. I will definitely sign up if plans change

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I’m gonna wake up early to do this. Like, really early. Can I do MVY-HPN, JetBlue E190?

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A bit early for me, will try my best to join this spooky fly

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I can do this!

I mean the event is a whole day, you can do the flight at like noon your time and the event would still continue

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I know I’m an early bird anyways though

Yeah. When it was first created though, it was not all day, just a morning period.

I’ll take off and then leave. @Gonzo, what is your timezone?

Sign me up please!

I am Eastern time zone.

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so your also going to wake up early?

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Sign me up for KBOS A320

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ill be doing jetblue A320 to KDCA

Its the KHPN fly in, so it would be KDCA - HPN.

I’m in the eastern to

I’m coming with Flex Jet from KSGR

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NetJets 1479 from KLAS to KHPN Challenger 350

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I used to be the same especially during weekends and also when I was in high school during weekdays where I have to get up at 6am, it was often so hard for me to wake up every Monday morning at 6am for school

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