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Day Trip to Sleepy Hallow and Tarrytown, NY With A Dog

Oct 2, 2024

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Headless Horseman Statue, Sleepy Hallow
Headless Horseman Statue, Sleepy Hallow

It’s time for a fall adventure to Sleepy Hallow and Tarrytown in the Hudson Valley.

 

Sleepy Hallow was the inspiration behind Washington Irving’s The Legend of Sleepy Hallow. It is a ghost story of a restless ghost soldier who was decapitated by a cannonball in a battle during the Revolutionary War. This Headless Horseman rides nightly through Tarrytown searching for his head.

 


At Sleepy Hallow Graveyard
At Sleepy Hallow Graveyard

Best time to visit: October, Halloween

How to get there from NYC: I recommend driving, it is a quick 30-mile/40-minute drive north and makes getting around and visiting many of the attractions efficient

Alternative option: Metro-North Railroad – Hudson Line, Philipse Manor station stop, approximately 1 hour. If you decide on this option, bring walking shoes or take a taxi to get around to all the attractions

 

Below are a few highlights and must-see spots from our adventure.



The Old Dutch Church and Burial Ground and Sleepy Hallow Cemetery.

  • This cemetery is the final resting place of Washington Irving, the Vanderbilts, William Rockefeller, and Van Tassels



Headless Horseman Bridge.

  • This is one of the most popular sites to see. The bridge is over the river on the cemetery grounds

  • In The Legend of Sleepy Hallow, the Headless Horseman chases Ichabod Crane toward a wooden bridge



Headless Horseman Sculpture

  • The giant metal sculpture of Irving’s Headless Horseman chasing Ichabod Crane is located outside the cemetery

Go into town, Main Street has clothing boutiques, vintage stores, and restaurants

 


Philipsburg Manor
Philipsburg Manor

Honorable mentions:

  • The Philipsburg Manor was the inspiration behind the Van Tassel Manor in Washington Irving’s The Legend of Sleepy Hallow. Today it is a history museum where visitors can explore the manor house

  • The Great Jack O’ Lantern Blaze hosted at the Van Cortlandt Manor showcasing a stunning 7,000 hand-carved pumpkins

 



Other fun ideas from our adventure:

  • Tray some locally brewed beers, I grab, the Tarrytown Dubbel Duncan’s Abbey a Belgain-style dubbel ale

  • On our way back to NYC, we stopped by Hudson Farmer & the Fish for outdoor dinner at sunset on the Hudson River


What other spots do you recommend on a day trip with a dog to Sleepy Hallow? Comment below.

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