Top things to see on your Sleepy Hollow trip

Located along the banks of the Hudson River, just a short drive from New York City, is where history and legend intertwine. Sleepy Hollow is a village located in New York State’s Hudson Valley and is known as the setting of “The Legend of Sleepy Hollow.” As you enter this charming town, you'll find yourself surrounded by history and Washington Irving's enchanting tales.

If you're visiting for the first time, you're probably looking for a list of the must-see parts of the town. Let me break it down for you.

Sleepy Hollow is a picturesque little town full of charm and history and is a nice place to spend a free weekend. The fall season is the busiest time to visit but visiting the first weekend in October wasn't too bad in terms of crowds. If you do choose to visit during the fall season, make sure to wander around the town shops and see the Halloween decor that adorns the storefronts and sidewalks.

Top things to see:

1. Sleepy Hollow Cemetery

One of the most visited parts of Sleepy Hollow is the Sleepy Hollow Cemetery. This is where the famous Washington Irving is buried. This cemetery is quite large so if you plan to visit and you would like to walk around, prepare to do quite a bit of walking up and down hills. There are areas where you can drive your car through the cemetery but there are areas where the roads are blocked off and are walking only. The front part of the cemetery is much older and does not have car accessible roads so you'll have to walk around. The back part of the cemetery is much more open and has roads you can drive on. There are some parking spots but depending on the time of year you visit, it might be harder to find a spot. If you plan to visit Sleepy Hollow in late September and October, you will encounter a lot more people than usual.

Make sure to grab a map from the visitors center. The map will give you a list of some of the famous people buried there. The biggest one is Washington Irving. He is located towards the front of the cemetery, only a small walk from the Old Dutch Church. A lot of people stop to take pictures here.

Washington Irving gravesite

While you're in the cemetery, you can visit William Rockefeller, Walter Chrysler, Andrew Carnegie, and many other grave sites. Also, make a stop at the memorial statue for fallen officers and soldiers of the Revolutionary War!

William Chrysler gravesite

Andrew Carnegie gravesite

2. The Old Dutch Church of Sleepy Hollow

The Old Dutch Church of Sleepy Hollow is located at the front of the Sleepy Hollow Cemetery. This church was built by Frederick Philipse in 1697. It's a small little church full of history.

3. Headless Horseman Statue

The Headless Horseman statue is located right near the sleepy hollow cemetery. It is located on a busy street so be aware of traffic when visiting. Stop by and take a picture!

4. The Headless Horseman Bridge

The Headless Horseman Bridge is located in the Sleepy Hollow Cemetery and is the bridge described in "The Legend of Sleepy Hollow." It's a fun little stop if you have the time. Be aware that the further into the fall season, the busier the bridge gets. Please also be respectful when visiting as it is a working bridge used by funeral processions and visitors.

5. Washington Irving's Sunnyside Estate

Washington Irving's estate is located alongside the Hudson River. It is technically located in Tarrytown but is a quick 4 mile drive from Sleepy Hollow. You will need to buy a ticket to visit the house and walk the grounds. Normally the price is $10 a person, however, it's $20 per person during October. Once we bought our tickets, we went down to the house where we got a quick history lesson on Irving and were allowed to enter the House. We were ushered from room to room by employees dressed in period pieces that gave info on each part of the house. Outside of the house tour, there are other storytelling events around the grounds. There's even a scavenger hunt for the kids.

Do note the website said the only available tickets and tours were only available every Thursday in October but we stopped by on a Saturday and were able to buy tickets towards the end of the day.

6. Philipsburg Manor

Philipsburg Manor is a restored 18th-century trading and milling museum that focuses on the lives of slaves. During the 17th and 18th centuries, the Philipse family owned 52,000 acres including a mill, farm, and large house near the Pocantico River. Today the Philipsburg Manor can be accessed via a tour. You can walk near the manor but in order to enter the building you will need to buy tickets. The tour is told through the perspective of the slaves that were kept by the Philipse family.

7. Kykuit, Rockefeller Estate

Kykuit is a 40 room historic house that was built for John D. Rockefeller. It's located in Pocantico Hills, only a 3 minute drive from the Old dutch cemetery. It was built between 1906 to 1913 and was the home for four generations of the Rockefeller family. There are multiple tours you can take through the house and the grounds. However, if you visit during October, you will need to buy tickets early. By early October every weekend was mostly sold out.

You can find them here: https://tickets.hudsonvalley.org/events.

8. Headless Horseman Hayride and Haunted Attractions

If you're visiting during spooky season, and you like a good scare, get tickets to this well known Hudson Valley Haunted Attraction. They have a hayride, corn maze, and 5 haunted houses to enjoy. You can buy tickets here: https://headlesshorseman.com/tickets. The event runs select nights from the end of September to the end of October.

Whether you come to relive the timeless tale of the headless horseman or simply to soak in the serene atmosphere, this village offers a unique blend of old-world charm and captivating stories. So, whether it's the crisp fall air, the history, or the thrill of the unknown that draws you here, one thing is certain: Sleepy Hollow will weave its spell around you, and you'll leave with memories that linger long after your visit has come to an end.

Have you ever visited Sleepy Hollow? What other things do you consider must-sees?