The Legend of Sleepy Hollow, NY

Immortalized in Washington Irving’s famous tale, the village of Sleepy Hollow is renowned for its ghosts and the haunting atmosphere that pervades the imaginations of its inhabitants and visitors. Located on the east bank of the Hudson River, Sleepy Hollow is an hour north of NYC and 4-1/2 hours from Frederick County, Maryland. Perhaps the most spectacular reason to visit Sleepy Hollow Country is the wildly magical Jack O’Lantern Blaze, where over 7,000 pumpkins set in an 18th-century landscape have been breathtakingly carved, illuminated and built into every shape possible.

“The chief part of the stories, however, turned upon the favorite specter of Sleepy Hollow, the Headless Horseman, who had been heard several times of late, patrolling the country; and, it was said, tethered his horse nightly among the graves in the churchyard.”

Washington Irving, The Legend of Sleepy Hollow

October is an exciting time to visit Sleepy Hollow. There are haunted hayrides, gothic mansions, blazing pumpkins, live music, a live story at the home of Washington Irving and of course, the Headless Horseman. If your visit includes the second weekend of October like ours did, the Sleepy Hollow Street Fair is where you will find food, music, local retailers, arts & crafts.

All of the rooms in the Tarrytown area were booked by the time we planned our visit so we stayed in Nyack, NY, across the Hudson River and about nine minutes from Sleepy Hollow. You have to take the Governor Mario Cuomo Bridge to get to the other side of the Hudson River but the bridge is gorgeous. If you travel over it at night, the NYC skyline provides a magnificent view that looks worlds away from this sleepy area.

My youngest daughter said she’s always wanted to visit the Statue of Liberty so we made a stop at Liberty State Park in Jersey City, NJ on our way home. NYC is less than an hour’s drive from Sleepy Hollow. I highly recommend catching the ferry from the NJ side! It was an easy in and out, and $7 for all day parking. There’s a beautiful memorial called “The Empty Sky” dedicated to 9/11 where the view of the Twin Towers once stood.

We loved this visit to Sleepy Hollow so much that we’re already talking about making this an annual October tradition, and slipping in a day stop in the Big Apple seems easier for us than planning a whole trip there.

Maybe next year, we’ll run into the headless horseman.

2-Day Itinerary With a Kid

Day	To	From	Mode	Departure Time	Arrival Time	Trip Notes
1 Fri	Nyack, NY	Frederick County, MD	Car	4:00PM	9:30PM	The drive on a Friday evening was surprisingly easy. It should have taken us 4-1/2 hours but we stopped for dinner in Gettysburg, PA.
	The Great Jack O’Lantern Blaze Hudson Valley, NY	Nyack, NY	Car	10:00PM	10:15PM	A must do! 7,000 pumpkin works-of-art along the Hudson River – we didn’t know what to expect but everything was top notch! We loved it so much that we’re hoping it can be a yearly October tradition.
2 Sat	Nyack Diner Nyack, NY	Our hotel	Car	8:00AM	8:05AM	A great little breakfast spot with a large breakfast menu and good service.
	Sunnyside, the home of Washington Irving Tarrytown, NY	Nyack, NY	Car	8:30AM	8:40AM	We stopped to see if we could get a glimpse of the home and its grounds but you have to buy a tour ticket to see it. We would have booked The Legend of Sleepy Hollow story event on the grounds but we didn’t want to miss our Statue of Liberty ferry tickets.
	Downtown Sleepy Hollow, NY	Tarrytown, NY	Car	9:00AM	9:15AM	We parked at Sleepy Hollow High School, home of the… you guessed it – headless horsemen, and took our own walking tour. The town is small enough to be able to do this but wear comfortable shoes!
	Old Dutch Cemetery, Headless Horseman Bridge	Downtown Sleepy Hollow	Walk	9:30AM	10:00AM	I’m not usually a fan of stopping in to visit a cemetery but this cemetery established in 1658 is so full of history, not to mention Washington Irving wrote that the headless horseman can be found here at night. William Rockefeller, Andrew Carnegie and Alexander Hamilton’s daughters are among the notables buried here. You’ll find historical plaques referencing the headless horseman bridge on the way back and the Headless Horseman sculpture.
	Sleepy Hollow Street Fair	Old Dutch Cemetery	Walk	10:30AM	12:00PM	I love when a town pays homage to its history. The headless horseman can be found everywhere in Sleepy Hollow, even on their ambulances and fire trucks! The Street Fair was nice, but I would have preferred more local artisans. We got a pickle on a stick and picked up a few treasures before walking down to the river for a great view of the Governor Mario Cuomo Bridge.
	Liberty State Park Jersey City, NJ	Sleepy Hollow, NY	Car	1:00PM	1:45PM	Lots of nice surprises at Liberty State Park including The Empty Sky memorial and Lady Liberty laying on her side. It’s so much easier to catch the ferry from here instead of Battery Park in Manhattan.
	Ellis Island and the Statue of Liberty	Liberty State Park	Ferry	2:00PM	2:15PM	A must do bucket list item! Be sure to book crown tickets way in advance though – these were all sold out for us.
	Home	Liberty State Park	Car	4:30PM	9:00PM	Sticking to the New Jersey side of NYC makes for a really easy drive home.