Southern New England Outdoor and Nature Site: Sleepy Hollow, NY

Rip Van Winkle
This Sycamore is more than 250 years old. It
is older than the United States and was on
the property when Washington Irving bought it.

I will be starting this posts the same way I do with many others...I have wanted to go to (fill in the blank) for years. It has been on my bucket list for a very long time. This is true of this post but for reasons beyond my control, I just never seemed to get to Sleepy Hollow until this weekend. Multiple times we planned on going to Sleepy Hollow and the weather would be rainy all weekend. Another time, we hoped to go last Columbus Day weekend and the campground was full. Luckily, this was the weekend.

You probably know of Sleepy Hollow because of the Washington Irving short story "The Legend of Sleepy Hollow" about Ichabod Crane and the Headless Horseman. Irving lived in Sleepy Hollow, NY which is a village of Tarrytown. Another part of Tarrytown in a village named after Irving named Irvington. Irving wrote many tales about the area including a history of the Hudson Valley and more famously Rip Van Winkle.

Probably a more accurate
depiction of Rip Van Winkle

Irving was a nomad and travelled much of his life. He finally settled down in Sleepy Hollow at the age of fifty two. He bought a nice property along the Hudson and built a house which he named "Sunnyside". He was a romantic and designed the house with many European style influences. He had the grounds laid out to be parklike with paths weaving around the hills. He built a small pond and a small stream.

We only spent Sunday and Monday in the Hudson Valley. Laurie and I went on two tours, more on those below. We stayed twenty miles north of Tarrytown in a town called Peekskill. Peekskill is where the TV show "The Facts of Life" took place. Incidentally, Ossining is a town between Tarrytown and Peekskill. Don Draper, a character from Mad Men lived in that town. Obviously, many movies have been about Sleepy Hollow so we spent a lot of time in places where television shows were filmed. The place we stayed was called Inn on the Hudson. It wasn't quite on the river but had a commanding view of it. Almost across the street ( you would need to drive) was Peekskill Park where there is a boat ramp and river access. Inn on the Hudson was $107/night. The rooms were clean but one electrical outlet was broken. Photos of each thing we did below the text.

We left Sunday morning and came back Monday evening. The first thing we did was go to a farmer's market in Irvington. I really wanted to feel "old New York/New England" so the farmer's market was something I was looking forward to. I only bought a crepe for breakfast and some unpasteurized cheese. None the less, I was happy we went.

Next we went to a tour of Sleepy Hollow Cemetery. Sleepy Hollow has many different types of tours. We chose the one hour "Original Knickerbocker Tour". Our tour guide was a high school history teacher named Tal. He was great. We stopped at Washington Irving's grave along with many others. Tal told us a ton of facts about Irving, gravestones, and a few of the residents of the cemetery.

This is a chamber from the tomb below

This was a storage tomb. The dead were put in here in the winter when the ground was frozen.
In the spring they would be removed and buried in their plots. We got to go inside

Washington Irving's grave between the two flags. He was a veteran of the War of 1812

After our Knickerbocker Tour Laurie and I went around the cemetery looking for historical figures. The cemetery has a lot of famous residents and it would have taken hours to find them all. We just went to the graves of Andrew Carnegie, Walter Chrysler, and William Rockefeller, a partner in Standard Oil with his brother John D

Carnegie's grave is by far the most humble.

Rockefeller Mausoleum

Chrysler Mausoleum

One thing we wanted to do was find real places that Irving woven into his stories. The most famous would be the Sleepy Hollow Bridge that the Headless Horseman rode over to slay old Ichabod Crane. The bridge no longer stands over the river. There is a plaque where the bridge used to be. Now a large asphalt bridge is in it's place. There is a bridge in the cemetery a quarter mile from the original bridge that now has the name Headless Horseman Bridge

The new Headless Horseman Bridge

Another famous location from the story is the Old Dutch Church. The church was built in 1697! Irving knew about these places because he spent time here as a boy when there was a Yellow Fever epidemic in New York City.

After visiting the cemetery we went to the motel. It was hot and showers were needed. We made supper and just watched some television for an hour then went to Peekskill Park. I saw a guy catch a White Sucker and immediately put in in a bucket to take home.

View from Peekskill Park and a spot on my lens!

Monday morning we got a "bag breakfast from Inn on the Hudson. The breakfast included a small OJ, granola bar, small muffin, and a yogurt. From there we took a few photos of the Hudson River at Peekskill Park.

We drove down to Irving's home the "Sunnyside" We took the 11 am tour which lasted about an hour. Again, it was great. Our guide told us about the home and of course, Washington Irving. After the tour we were allowed to walk the grounds. There were paths through the woods. We stopped at the small pond. It rained a little and we took shelter in the gazebo. There were apple trees on the property. I may or may not have snagged one and ate it. There was a beautiful garden with the tallest corn I've ever seen. There were beautiful flowers and pumpkins.

View of Irving's house and the Hudson

The ivy growing on Irving's house was planted by him. It is two hundred years old

A close up of the 250 year old Ivy plant

As previously stated, I could not guarantee this apple made it safely through the day

When the railroad came through, part of Irving's land was taken through immanent domain

I have never seen corn this tall

After the tour, we made a quick stop at Sleepy Hollow Cemetery for a few more photos and came home.

There are other things to do in Sleepy Hollow and the Hudson Valley. There are other mansions to our including the Rockefeller Estate. There are many parks and places to hike. There are events including farmer's markets, concerts, and festivals every weekend. I'm not too interested in mansions and I hike a lot. We really wanted to learn about Irving and the legends of the area.

If you go...

Tarrytown is not quintessential New England (yes I know it is New York). The town is kind of built up. You'll find pizza places, drug stores, and all other stores in town. But it looks like any other strip mall or store fronts. It is after all, a suburb of NYC. Though there are town commons and parks, do not expect the falling of autumn leaves in front of a big white church. The façade is kind of run down.

I could write a million things to help you plan your trip, but the website https://visitsleepyhollow.com/ has all the info you would need. I spent countless hours over the past two years deciding what to do. The most important page was the calendar of events. If you want to go to the Sunnyside, you have to go to their website, because it does not seem to be on the visitsleepyhollow website.

More photos below