10 Things to Do in Sleepy Hollow, NY

Sleepy Hollow, NY is the small, quaint town that was the inspiration for Washington Irving’s story The Legend of Sleepy Hollow, released in 1820. “The Legend of Sleepy Hollow”, for those of you who are not familiar with it (although I’m sure the number is very low), tells the story of Ichabod Crane and his attempts to win the heart of Katrina Van Tassel. Perhaps one of the most well-known characters in the story is the Headless Horseman who spends his days hunting for his head. I would recommend looking into the story or refreshing yourself before heading out to Sleepy Hollow. Anyways, now on to all this little village has to offer…

1-Visit the Sleepy Hollow Cemetery

The Sleepy Hollow Cemetery is the final resting place of Washington Irving and also home to the Headless Horseman Bridge replica. Other notable burials in the Sleepy Hollow Cemetery are Andrew Carnegie and William Rockefeller. Tours are held in select months throughout the year. Before traveling to Sleepy Hollow visit their website at http://sleepyhollowcemetery.org/events/tours-and-events/ to see if any are offered during your travel dates. You can also tour the cemetery on your own between 8:30am and 4:30pm daily.

2-Visit the Old Dutch Church Burying Grounds

The Old Dutch Church and Burying Grounds are the ones famously featured in “The Legend of Sleepy Hollow”. The Old Dutch Church is also one of the oldest churches in the state. In the month of October the church offers live readings/shows of “The Legend of Sleepy Hollow” with tours of the church and burying grounds. Year-round you can walk the grounds of the church and burying grounds. It will feel like the pages of the story are coming to life!

3-Visit the Phillipsburg Manor

The Phillipsburg Manor is a 1750 English manor that once housed African slaves. The manor was once a milling an d trade complex. Today it is a living history museum and you can tour the grounds. Timed tours are offered daily at $12 for adults, $10 for seniors and young adults 18-25, and $6 for children 3-17. In October the manor transforms into a haunted house-Headless Horseman Hollow. Unfortunately when we visited this event was not going on., we missed it by a day!

4-Visit the site of the Headless Horseman Bridge

While the Sleepy Hollow Cemetery is home to a replica of the Headless Horseman Bridge, it is not the original. The original bridge that was the inspiration for the story is no longer standing. A concrete bridge was constructed where the Headless Horseman Bridge previously sat in 1912. However, there is a sign marking it’s location. It is right outside the Old Dutch Burying Grounds. Simply take the less than a minute walk and you will come upon the sign that marks the spot.

5-Stop for a photo of the Headless Horseman Statue

Be careful with this stop as the statue is in the center of a busy highway. However, it is worth making the stop to see. It is only a couple minutes walk from the Old Dutch Burying Ground, so after visiting the site of the original Headless Horseman bridge, continue and you will shortly find the statue.

6-Visit the Sleepy Hollow Lighthouse

The Sleepy Hollow Lighthouse, built in 1883, sits inside Kingsland Point Park. The park itself is a nice place to visit and enjoy a relaxing afternoon with great views of the Hudson River and the Tappan Zee Bridge. The park has a small area of water access as well, but the sand is littered with debris. Park in the parking lots and take the short, five-minute walk over to the lighthouse. The lighthouse itself is rather small, but it is still worth the trip. The path from the park leads right up to the bridge that you can cross and come right to the foot of the lighthouse.

Tours of the lighthouse are offered, but days and times vary depending on the time of year. Be sure to check ahead and see if the lighthouse will be open when you go (but I would still recommend stopping even if it will not be).

7-Visit Sunnyside

Sunnyside is the cottage-like home of “The Legend of Sleepy Hollow’s” author Washington Irving. Timed tours are offered daily during the warmer months and, like many other locations in Sleepy Hollow, Sunnyside offers special Halloween themed events in the month of October.

8-Spend some time strolling and shopping along Main St. in nearby Tarrytown

Main St. in Tarrytown offers many local vendors and restaurants and gives you the small town feel. We did not have time to stop and eat while in Tarrytown, so I can not give recommendations there, but the food smelled delicious and the street was live with people coming and going from the restaurants despite the rain. Stop and pick up some hand made crafts in one of the many shops.

9-Visit the Tarrytown Music Hall

The Tarrytown Music Hall has a rich history and is now believed by many to be haunted. The Music Hall was built in 1885 and has served as an entertainment venue for some of the village’s most famous residents, including the Rockefellers, served as a venue for several national causes, served as a movie theater, and now as a performing arts center. The Music Hall is also believed to be haunted and ghost tours/paranormal investigations are offered on select days. Visit https://tarrytownmusichall.org/ for information on ghost tours and a list of currently scheduled shows.

10-Visit the Rockefeller State Park Preserve

The Rockefeller State Park Preserve is a 1,400 acre nature preserve that offers miles of hiking trails along with seasonal activities, such as bird watching, fishing, cross-country skiing, sledding, and horseback riding. It is a great escape for a relaxing, quiet afternoon and will bring you face to face with nature.

Sleepy Hollow has even more to offer during the fall months as the village gears up for Halloween. The Great Jack-o-Lantern Blaze takes place beginning at the end of September through the middle of November. The event features over 7,000 pumpkins that are hand-carved. Unfortunately the blaze was cancelled the night that we were in Sleepy Hollow due to heavy rains and flash flooding.

The fun does not stop there. Sleepy Hollow also offers special readings of “The Legend of Sleepy Hollow” and tours of story related locations throughout the month of October. For more information on the special events of Sleepy Hollow visit https://hudsonvalley.org/article/top-10-halloween-attractions-in-sleepy-hollow-country/

10 thoughts on “10 Things to Do in Sleepy Hollow, NY

  1. This is so eeriely mesmerizing! I’ve never seen Sleepy Hollow documented like this and for some reason, I’m itching to visit now! 😂 🤣

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  2. I love Washington Irving and the Headless Horseman. I would love to visit Sleepy Hollow mostly for the replica bridge. I would obviously have to take a picture with the Headless Horseman Statue as well.

    Like

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