Sleepy Hollow… The Legend of the Long Walk

The Legend of Sleepy Hollow by Washington Irving is one of my favourite stories. I have read the book, watched the movies, the TV show and even seen the Disney cartoon. So when Dawn suggested that during our recent visit to New York that we could visit Sleepy Hollow I was very excited.

For those of you who don’t know what The Legend of Sleepy Hollow is, it is the story of Ichabod Crane and his experience with a headless horseman. There have been many variations of the story but they all essentially tell the same story.

We decided that we would go to Sleepy Hollow on the Saturday afternoon, we would get the train and then visit the areas we had heard about.

During our research we found that there were a few things to see and that a local restaurant even served a Headless Horseman burger.

When we arrived at Grand Central Station we were informed that Sleepy Hollow doesn’t have its own train station, so we got a ticket to the nearest station which is at Tarrytown. The journey takes around an hour and to be honest passes through some beautiful countryside.

We arrived at Tarrytown and set out to walk to Sleepy Hollow, I had downloaded a map but we weren’t sure where to start so we asked a few people and were given general directions. We soon arrived in the Tarrytown centre, this area is very pretty and looks like a traditional small town complete with boutiques and coffee shops. even a farmers market in the local park. However, as Tarrytown wasn’t our destination we continued on.

We seemed to be walking for a very long time and finally we passed the ‘Welcome to Historic Sleepy Hollow’ sign’, that is so famous in all the literature.


One of the things we found was that there are not many (i.e. none) signs to indicate the way to the Old Dutch Church and Sleepy Hollow Graveyard.

We did, however, see a sign that indicated the way to the town centre, unfortunately we didn’t know that the church and graveyard were not in the actual town centre. After walking for quite a while and asking directions from many people who didn’t seem to know their own town, we decided that it was time for a drink. Totally by chance I had noticed a restaurant we had passed earlier so we decided to go in there and re-group. It was a very hot day and at this point we had been walking for well over an hour.

The restaurant wasn’t busy so we sat down and and ordered drinks we perused the menu and discovered that this was the restaurant with the Headless Horseman burger. I decided that this was what I fancied and suddenly was very hungry. We had only had a quick Starbucks for breakfast. The burger was very nice and came with a side of chilli.


The waitress in the restaurant was excellent and when we asked the directions to the church and graveyard she actually came and wrote down the exact directions for us. It turned out that we were on the right track but had turned off the main road too early.

Once we were fed and watered onward with our quest we went. After a further 15 – 20 minutes of walking we finally saw the Old Dutch Church ahead.

On arriving at the Church we walked up and found the graveyard and the grave of Washington Irving himself.

We walked back towards the Philipsburg Manor House which is a former mill and now a museum. From here you can visit Kykuit, the John D Rockefeller Estate, which is found in the nearby town of Mount Pleasant. Tickets and a bus can be obtained from the shop to visit this house. We didn’t visit Kykuit on this occasion but maybe would be interested in the future.


We knew that there was a statue of the Headless Horseman in Sleepy Hollow and after visiting the Old Dutch Church of Sleepy Hollow and Graveyard and the Philipsburg Manor we were surprised that neither of these attractions appeared to house the statue. We decided to ask one of the ladies working in the shop. She informed us that the statue was between the Church and the Manor near the Headless Horseman Bridge. We realised that we had actually seen the statue but hadn’t felt that this was the official statue.

The Headless Horseman statue is a bronze sculpture on an island in the middle of the road, we had expected it to be an actual statue but it isn’t. This doesn’t make it any less interesting to look at.


Whilst we both felt that visiting Sleepy Hollow was an enjoyable day, we agreed that maybe we would do a few things differently next time. For example, we wouldn’t try and walk from the Tarrytown station to Sleepy Hollow. To be honest by the time we had found the Church and graveyard we hadn’t enough energy left to actually enjoy it fully. As it was June when we visited we did wonder if Sleepy Hollow was maybe more interesting in the fall towards Halloween.

Have you been somewhere that was different from what you were expecting? Would you visit there again?


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