THE REAL SLEEPY HOLLOW + TARRYTOWN: New York Charming Travel Guide

The real town of Sleepy Hollow, where legends and lores are born.

There is an old dutch village upon the historic Hudson River where a legend was born. The legend of the Headless Horseman and an uncertain fate of young school master Ichabod Crane.

The first time I realized that Sleepy Hollow was real was when we for the first time suddenly drove through it.

Sleepy Hollow is a place where the lines are blurred between history and myths, thanks to author Washington Irving. A place where every day seems to be Halloween, click the video below and we’ll show you around our favorite haunts!

Why not begin your day at the Sleepy Hollow Cemetery where you can wander for hours and dreaming up all kinds of stories, or if you prefer to take a nighttime lantern tour.

Make your way to the Headless Horseman bridge and listen to the sound of the babbling brook, the same sound it would have made as Ichabod Crane heard on that fateful all Hallow’s eve.

The original bridge would have been located a little farther up the stream next to the Old Dutch Church. Which is where we are headed next!

But on the way we must pay a visit to the legend himself, Washington Irving, where every October a pumpkin ordains his resting place. You can also visit his home “Sunnyside” in Tarrytown.

Here we are at the Old Dutch Church, built in 1685, one of the oldest in New York State! In it’s church yard is where the residents are buried such as the Van Tassel family who inspired Irving’s tale. Take a scavenger hunt in search of the unmarked grave of the Hessian soldier.

Catch an appearance of the Headless Horseman walking among the graves during the Old Dutch Church festival which is held weekends in October! Stay for an evening performance of the legend inside the church.

Or head across the way to Philisburg Manor to experience what life would have been like in the village in the 1700s. but you better be gone by dark or you may loose your head at the Horseman’s Hollow!

Sleepy Hollow main street is just up a ways from there everyone seems to be in the Halloween spirit! Stop by the street fair mid October weekends.

Definitely make some time in your visit to visit some stately homes in the area like Kykuit: Rockefeller Estate or Lyndhurst Manor.

Head on over to Tarrytown for some treats! Treat yourself to some souvenirs. Then, Tea time or ice cream and dinner at Horsefeathers!

Take an evening stroll down the main street and admire the stunning architecture. Admire the old churches by moonlight. Feel the haunting chill in the air in a town caught between myth and reality.

Thank you for coming along on another charming adventure with us!

-Lindsay & Jonas

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