Sleepy Hollow New York: The Headless Horseman’s Town

Did you know Sleepy Hollow is 50 minutes from Manhattan by train from Grand Central Terminal?

That's right, the town that inspired Washington Irving's famous story is very close to Manhattan.

The tale is an American literary classic, brought to the screen by Disney (The Story of Ichabod Crane and the Headless Horseman, 1949) and by Tim Burton's Sleepy Hollow (1999).

What to Do in Sleepy Hollow

October is the best time to visit Sleepy Hollow, when the town fills up with pumpkins, events and Halloween decorations.

The town was originally called North Tarrytown, but in 1996 it officially changed its name to Sleepy Hollow, in tribute to Irving and the fame he brought it.

When you visit Sleepy Hollow, you'll see the places Washington Irving described in The Legend of Sleepy Hollow (1820) and other stories like Rip Van Winkle.

These landscapes were very familiar to Irving, who spent a good part of his life in a mansion on the banks of the Hudson.

Here's a rundown of the spots in the town of the Headless Horseman you shouldn't miss:

1. The Old Dutch Church

The Old Dutch Church is the oldest church in New York State still standing.

It was built in 1685 by the owners of Philipsburg Manor, an estate that now works as an interactive museum right across from the church.

Next to the church you'll find an old graveyard (the Old Dutch Burying Ground), with some Dutch colonists' graves that were already there before the chapel was built.

This church appears in Washington Irving's story and in Tim Burton's film too.

Hours

It only opens on weekend afternoons in summer and winter. But you can wander the grounds freely.

Address

430 Broadway, Sleepy Hollow

2. Sleepy Hollow Cemetery

Very close to the church is another of the most visited spots: Sleepy Hollow Cemetery.

Washington Irving rests there, along with other blue-blooded New Yorkers like Andrew Carnegie, Walter Chrysler and Elizabeth Arden. Ring a bell? And of course, on top of a hill stands the Rockefeller family mausoleum, one of the first families to build their mansion beside the Hudson River.

The thing is, the beautiful landscapes of the Hudson Valley drew New York's magnates out here to build their country estates.

A fun fact: Washington Irving took the names in his story from the old headstones in Sleepy Hollow Cemetery (the oldest ones sit next to the Old Dutch Church).

As you walk around, you'll notice several are written in Dutch. That's because the town, like much of New York State, was a Dutch colony before it was English (New York, for example, was once New Amsterdam).

Hours

You can explore the cemetery on your own between 8:30 am and 4:30 pm, and admission is free.

There are guided tours, which you need to book in advance on their website.

Address

540 North Broadway, Sleepy Hollow

You can walk from town to the main entrance, but the sidewalk along the road isn't well maintained.

Our advice is to take a taxi or walk through the grounds from the Old Dutch Church.

3. Philipsburg Manor

Philipsburg Manor was the estate of powerful Dutch merchants, the Philipse family.

Today you can tour their three-century-old house (tickets must be bought in advance), where you'll get a look at the region's past and at how the European colonists who made America their home lived, enslaved people included.

The guides at this house museum dress in period clothing.

It's open from May through mid-November, Wednesday to Sunday.

Guided tours run between 10 am and 3:30 pm.

Address

381 North Broadway, Sleepy Hollow

Prices range from $13 to $18. You can book your ticket and see more details on the attraction's page.

4. Washington Irving's House

In Tarrytown, just south of Sleepy Hollow, sits Washington Irving's house, with a spectacular view of the Hudson River. It's called Sunnyside, and you can tour it by booking in advance on the Historic Hudson Valley website.

The house is a historic landmark. Inside you'll see furniture, books and other belongings of the first American writer to earn international recognition. Irving influenced other major authors like Edgar Allan Poe (whose cottage in the Bronx you can also visit!) and Nathaniel Hawthorne, the author of The Scarlet Letter.

Hours

Open from May through mid-November, Wednesday to Sunday.

Guided tours run between 10 am and 3:30 pm.

Address

89 West Sunnyside Lane, Tarrytown

Price

Adults $12 / 65+ $10 / under 17 $6 / under 3 free

5. The Rockefeller Estate: Kykuit

Want a glimpse of the Rockefeller way of life?

When you visit Sleepy Hollow, don't leave without seeing Kykuit, the mansion where four generations of Rockefellers ran their empire.

It's a trip well worth making, and one to plan ahead for, since the guided tours have limited spots.

Given this family's role in building the modern New York we love, we gave Kykuit, the Rockefeller mansion, its own post.

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As you can see, visiting Sleepy Hollow isn't all headless horseman. There's plenty to see, so it's worth a day or two.

If you're short on time, you can fit two attractions into one day. Figure on 2 hours of travel, plus about 2 hours at each attraction, plus the walking.

You can pair this trip with other day trips north of New York that we'll be covering soon.

How to Get to Sleepy Hollow from New York

Sleepy Hollow is 50 minutes by train from New York.

The trains run on the Metro-North Hudson Line, departing from Grand Central Terminal toward Tarrytown, which is where you get off.

There are several departures a day, and you can check them on the MTA website.

Once you reach Tarrytown station, you can grab a taxi to whichever spots in town you want to see, or just walk, since everything is close by (plan your route on Google Maps).

More day trips near NYC

If you are already in New York, you can visit other interesting destinations in a single day. Check them out in our guide to day trips from New York.

I recommend taking a road trip from New York to Philadelphia. I put together an itinerary that also takes you through the most important towns in Pennsylvania's Amish communities. It's a trip back in time!