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Pro Tip: While not officially in Sleepy Hollow, Lyndhurst Castle (Mansion) is just 2 miles away. You’ll see guides in period costumes and experience what Irving’s life would’ve been like. Make sure to wander the grounds to admire the landscaping. He bought the two-room Dutch house in 1835 and extensively remodeled it. Washington Irving’s Sunnyside Estate is an important stop in Sleepy Hollow. Photo Credit: Kenneth Sponsler / Shutterstock 6. The museum now depicts the history of the slaves during that period.

In 1750, the manor was a working farm that relied on the labor of 23 slaves, making the Philipses one of the largest slaveholding families in the northern colonies. His family ended up owning more than 50,000 acres in the Hudson Valley. Frederick Philipse came to the Hudson Valley in 1653 as a carpenter. Stop by the Philipsburg Manor which also makes an appearance in Irving’s story. Photo Credit: Sue Davies / Travel For Life Now 5. It’s on Route 9 right across from the Philipsburg Manor. It’s a depiction of the moment in Irving’s book when the headless horseman throws the pumpkin at Ichabod Crane. Spend a few minutes taking a photo of the Headless Horseman Sculpture. Photo Credit: Sue Davies / Travel For Life Now 4. Pro Tip: If you’re short on time or not a diehard Irving fan, we recommend skipping this stop. Despite the lack of historical accuracy, this bridge is still a picturesque spot for a picture or selfie. The bridge over the Pocantico River where Ichabod Crane falls off his horse no longer exists. If you’re walking through the cemetery, take a detour to the bridge. Take A Photo At The Headless Horseman BridgeĪnother must-see location in Sleepy Hollow is the Headless Horseman Bridge. Photo Credit: Regina Ang / Travel For Life Now 3. You’ll see it right before you walk into the cemetery. If you are there when the church is closed, it’s still beautiful to see it from the outside. Pro Tip: The church is open for very limited hours on the weekends. The cemetery is the burial ground for the church. Still, with an active congregation, the church has been in continuous operation since the late 1600s. Ichabod Crane was in a mad dash to get to the church before the headless horseman got to him. See The Dutch Reform Churchįounded around 1685, the Dutch Reform Church is also featured in The Legend of Sleepy Hollow. Photo Credit: Sue Davies / Travel For Life Now 2. There are also guided tours, especially in October. It’s best to pick up a map so that you’re not wandering aimlessly. Pro Tip: The cemetery is very large, approximately 90 acres. You’ll also find memorials for Civil War soldiers. In addition to Irving, the cemetery is the final resting place for a number of historical figures, including Andrew Carnegie, Samuel Gompers, Elizabeth Arden, and Brooke and Vincent Astor. If you visit during the month of October, you will likely find throngs of young people in costumes in the cemetery. Don’t expect to get too close to Irving’s grave, though - it is protected by a fence. The cemetery is a prominent feature in The Legend of Sleepy Hollow and it’s a good place to begin your orientation to the town. Let’s begin with the Sleepy Hollow Cemetery. Photo Credit: Regina Ang / Travel For Life Now 1. Since Washington Irving and The Legend of Sleepy Hollow is so important to the town - once called North Tarrytown, the town changed its name to Sleepy Hollow in 1996 - we’ll start with the sites related to the story. Or do as we have done, go often and in every season. We recommend going more than once: first for Halloween, and then again as part of a visit to the Hudson Valley to enjoy the charm and historic sites at a less crowded and more leisurely pace. We’ve been to Sleepy Hollow many times and we never fail to find something new and interesting to do. If you love history, food, architecture, and nature, you’ll want to put Sleepy Hollow on your list of places to go.

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From the ghoulish events and lantern lights of Halloween to tours of historic estates and lazy summer day picnics in the park to experiencing The Legend of Sleepy Hollow by Washington Irving, Sleepy Hollow is full of things to do any time of the year.

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