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Following the Footsteps of Ichabod Crane: How to Staycation in Sleepy Hollow, New York

Following the Footsteps of Ichabod Crane: How to Staycation in Sleepy Hollow, New York

August 1, 2022 | share

Since so many visit Sleepy Hollow each year as part of their summer vacation exploration plans, it’s easy to see why residents at NorthLight might want to hold off on traveling this year to make way for their own summer exploration plan right here in our home town.

Here are just a few ways to get started on planning your own staycation right here in Sleepy Hollow, New York.

Van Tassel Homestead

Visit Van Tassel Homestead to see where Ichabod Crane began his walk home before encountering the headless horseman. The story’s Katrina is said to have lived at the Elizabeth Van Tassel house which was converted into a tavern before the Revolutionary War by the Mott Family. 

According to Historian Edgar Mayhew Bacon, Washington Irving was said to spend  a lot of time in this tavern where his sister was boarded by the Motts.

Philipsburg Manor

Today, the Philipsburg Manor house and mill have been restored to what it would have looked like in the 17th century. Set beside a pond, the mill was where Ichabod Crane was said to stroll with local girls. Interesting to note is that Frederick Philipse, who built the Old Dutch Church of Sleepy Hollow also constructed the Philipsburg Manor.

Patriots Park

Shared by Sleepy Hollow and Tarrytown, Patriots Park is where Ichabod Crane would first encounter The Headless Horseman on his way home that evening. Within the park is a monument marking the place where on September 23, 1780, three local militia men captures British spy John André, exposing Benedict Arnold and his plan to turn over West Point fortifications to The British.