Off The Main Roads….Tales of a Wandering Soul

Janice Krako/ October 22, 2013/ children, Family, Great Pumpkin Blaze, Headless Horseman, Hudson River, Hudson River Valley, Ichabod Crane, Kykuit, New York, Old Dutch Church, Phillipsburg Manor, Sleepy Hollow, Travel

I love getting out of the house to explore on the back roads 

I usually remember to take a camera in addition to a smartphone along. When you are exploring you never know what you will find!

Get off the Main Roads

Just north of New York City in Westchester County is a favorite ride for me especially in the Fall.  Get off the main roads of Interstate 287/87 and get on route 9A north and wind through the very scenic Hudson Valley.  It’s especially scenic this time of year with the trees in their autumnal splendor.  Maybe stop at a farm stand or pick some apples too or go antiquing.   All up to you!

  Fall Harvest

Nestled in the heart of the Hudson River Valley near Tarrytown is a quaint town known as Sleepy Hollow.

Until 1996 Sleepy Hollow was known as North Tarrytown. The whole Hudson Valley Region sits on the banks of the Hudson River and is ripe with Revolutionary War battles and history. The area was originally a Dutch settlement.  This is the same town where Washington Irving’s tale “The Legend of Sleepy Hollow” is set.  There are a number of interesting places to visit in Sleepy Hollow and surrounding areas such as Kykuit the Rockefeller family estate set on the Hudson River with it’s vast views of the river.

Hudson River Valley, NY

Sunnyside is the estate of Washington Irving and there are a number of other estates along the Hudson River.  Philipsburg Manor, which was a successful farming, milling, and trading, center owned by the Philipses in the center of Sleepy Hollow. If you have not had the opportunity to explore this are I would recommend you do make time for a visit.

Philipsburg Manor

Phillipsburg Manor Sleepy Hollow

The Legend of Sleepy Hollow

I will not tell you the entire tale here, just a snippet in case you have not heard or read it.   Ichabod Crane was a teacher who one very dark night was heading to a party at the Van Tassel’s residence hoping to woo Katrina Van Tassel. Suddenly out of the shadows came the Headless Horseman, local legend claimed him to be a fallen Hessian soldier buried in the nearby church cemetery in search of his head.  Ichabod was chased over a bridge trying to get away from the Headless Horseman.   The Horseman hurled his burning jack o’lantern head at Ichabod and chased Ichabod to the Old Dutch Church.

Sleepy Hollow Cemetery


The bridge is no longer in the center of town however the Old Dutch Church built in 1685 is.  This is the oldest church in all of New York State.  The cemetery surrounding the church is quite large and holds a great number of famous final resting places for business legends including Brooke Astor, The Helmsley’s, Andrew Carnegie, Rockefellers, and even Walter Chrysler founder of Chrysler Auto Company.   Tours are given of the church and cemetery including some at night, or, you can purchase a map and wander around yourself.


Sleepy Hollow Cemetery


Seasonal events hosted in Sleepy Hollow, which reference that legendary tale.

This year and every October Sleepy Hollow hosts a fabulous event The Great Pumpkin Blaze with more than 5000 blazing jack o’lanterns and is being held for 25 nights this year.  This is always a sell out event and tickets are necessary. It is mostly handicap accessible also.

Another seasonal event held yearly is at Phillipsburg Manor is Horseman’s Hollow.  

Ghosts and ghouls abound and will try and scare you out of your wits…. all in fun of course, and not for the faint of heart or small children.  Or perhaps Irving’s Legend would be an event you would like.   A reading of The Legend of Sleepy Hollow by a master story teller and held in the infamous Old Dutch Church where Ichabod fled. If you can not get there this time of year, how about a summer event like Pirates of the Hudson in early July, or Scrooge telling his story in the Old Dutch Church just after Thanksgiving and throughout December?  Family fun for sure!

This is a great area to visit for families, take photos, learn some history, step where many of the most famous people have the 19th and 20th century walked.   You do not always have to go far from home to have a great time.   There are many other towns along the Hudson River Valley on both sides of the river like Piermont….but that is a story for another day.

 Get out and explore!


Hudson Valley Events

Hudson River Views




Old Dutch Church***


Great Pumpkin Blaze**


Great Pumpkin Blaze**

*Kykuit   **   ***Sleepy Hollow Cemetery

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