Sleepy Hollow

On a recent Sunday morning a friend and I met at Grand Central Station to take an early train up to Sleepy Hollow. What better place to visit in New York at this time of year?

Grand Central Station on a Sunday morning.

A view of the colourful Palisades from the train.

Immortalized by Washington Irving in The Legend of Sleepy Hollow, this village on the Hudson River was originally called North Tarrytown. It wasn’t until 1996 that it officially adopted the name it was better known as—Sleepy Hollow. It's small and charming and yes, there are signs of Ichabod Crane and the Headless Horseman all around.

Philipsburg Manor House

We started off at Philipsburg Manor, a historical site that was once home to the Philipse family, one of the largest slave-holders in the Colonial North and staunch supporters of the crown. During the Revolutionary War, British Army General Sir. Henry Clinton was headquartered at the Manor where he issued the Philipsburg Proclamation, proclaiming all slaves owned by Patriots freed. After the war, the Philipses' land was confiscated and sold off into parcels. 

We soon turned our attention to all things Irving. After crossing the spot where the Headless Horseman Bridge once stood, we visited the Old Dutch Church of Sleepy Hollow whose groundbreaking occurred in 1685. It makes an appearance in the legendary story as does its small burial ground where the Headless Horseman is supposedly buried. At night, as the story goes, his ghost “rides forth to the scene of battle in nightly quest of his head.” The grounds are filled with the graves of the village’s early Dutch residents, many of whose names were inspiration no doubt for Irving.

"Don't blink."

A Celtic cross marks the grave of Andrew Carnegie.

Next door is the quite large Sleepy Hollow Cemetery where generations of famous New Yorkers are buried including Andrew Carnegie, Brooke Astor, Harry and Leona Helmsley, Walter Chrysler, and Washington Irving (naturally). There is even the grave of Dan Draper (oh, so close), the founder of the New York Meteorological Observatory in Central Park. The cemetery is huge (90 acres) so we did not see all of it but it is very pretty with one side dropping down to the Pocantico River. The cemetery is filled with a mix of simple headstones, statues, and mausoleums. One ring of angels immediately brought to mind the "Blink" episode from Dr. Who and gave me a chill.

Broken heart at Coffee Labs Roasters

Afterwards, we headed over to Tarrytown for lunch where we enjoyed the largest Greek salads I’ve ever seen at Lefteris Gyro and walked around, peeking into some of the antique shops and checking out the Music Hall. We stopped in at Coffee Labs Roasters for coffee and a sweet before heading back to the train and Manhattan. It was a nice break from the city and a great way to get into the Halloween mood (even if the weather was a bit too nice; a bit of fog would have suited nicely).

And if any of you are wondering, I have been watching the new Fox series Sleepy Hollow. It’s become my new guilty pleasure show (along with Scandal). It’s all over the place (a recent episode involved the Lost Colony of Roanoke, which was is in Virginia but okay) yet it's a lot of fun.

Photos by Michele.