Home Blog In the Footsteps of Washington Irving: A Literary Tour of Sleepy Hollow

In the Footsteps of Washington Irving: A Literary Tour of Sleepy Hollow

Photo credit - Shutterstock Nick L

Head about an hour north of New York City, and you will find the quaint town of Sleepy Hollow. Made famous by Washington Irving’s book, The Legend of Sleepy Hollow, this town is worth a visit. You will find it easily walkable as you explore sculptures, monuments, and real-world locations of places described in Irving’s book. The best way to see everything is to take a literary tour of Sleepy Hollow while staying at the Sleepy Hollow Hotel. 

Philipsburg Manor

Before exploring places of significance to Washington Irving, tour the Philipsburg Manor. The manor was home to an active mill during the 1700s when The Legend of Sleepy Hollow was set. Touring the estate immerses you in history to see what life was like for the characters of Irving’s book. Check the opening hours for the Philipsburg Manor when planning your visit, as the days and hours of operation fluctuate throughout the year.

 Sculpture of the Headless Horseman

Start your self-guided tour of Washington Irving’s Sleepy Hollow at the Headless Horseman Sculpture. It is a 300-foot walk from the Philipsburg Manor. It is also just over two miles and a less than ten-minute drive north from the Sleepy Hollow Hotel. 

The Headless Horseman Bridge

From the sculpture, you can walk to the site of the Headless Horseman Bridge. Washington Irving wrote about a bridge in his book that existed in Sleepy Hollow. Unfortunately, the original wooden bridge rotted away long ago. You will see a sign in the approximate location of the original bridge. In its place, there is a modern bridge that crosses the river. 

If you want to see a wooden bridge similar to the original, head toward the Old Dutch Church and Burying Ground. Once you go through the main gates, you can follow the path to a wooden bridge. It is the perfect spot for taking pictures. 

The Old Dutch Church and Burying Ground

After you visit the wooden bridge, head back towards the Old Dutch Church. This is where the headless horseman chased Ichabod in the book. Pick up a booklet at the church, and you can explore the grounds and their significance in the book’s events. You can visit the final resting place of the Van Tassels. You can also see the final resting place of Jäger’s headless corpse. It is theorized that this is where Irving got inspired by the character of the headless horseman. You must arrive before 4:30, as the grounds close at this time.  

Sleepy Hollow Cemetery

Next to the burying ground is the Sleepy Hollow Cemetary. Look for the signage leading you to Washington Irving’s burial site. You can pay your respects to this much-loved author. There are also several other famous resting places within this cemetery. 

  • William Rockefeller
  • Andrew Carnegie  
  • Walter Chrysler 
  • Elizabeth Arden 

The cemetery is open daily Monday through Friday from 8:00 AM to 4:30 PM and Saturday and Sunday from 8:30 AM to 4:30 PM.


No visit to Sleepy Hollow would be complete without a trip to Sunnyside. It is about 1.5 miles south of the Sleepy Hollow Hotel, making it a short five-minute drive. The Van Tassel family originally owned the property, and Irving bought it in 1835. He lived there until his death in 1859.  

Today, you can take a tour and see several rooms in the home with original furniture. His family also carefully added furniture replicas to keep the house as close to it as it was during Irving’s time. Check the estate’s website for hours to ensure you arrive during a time when the guided tours are offered. The hours can vary throughout the year, so planning in advance ensures you get to experience everything the home has to offer. 

Washington Irving Memorial

Once you visit his home, you can head over to the corner of Broadway and West Sunnyside Lane. Here, you will find the Washington Irving Memorial. The memorial includes a bust of Washing Irving between statues of Rip Van Winkle and King Boabdil. 

Take a Literary Tour of Sleepy Hollow

The town of Sleepy Hollow is rich in historical and cultural history. By taking a self-guided literary tour of Sleepy Hollow, you can discover the man behind the famous Legend of Sleepy Hollow. 

Book your stay at the Sleepy Hollow Hotel, and you are minutes away from Sleepy Hollow’s most well-known monuments and sites.