Discover Sleepy Hollow, New York

Print Friendly, PDF & Email

We recently spent a beautiful fall weekend hiking up in the Sleepy Hollow area of Westchester County. We toured Sleepy Hollow cemetery and Rockefeller State Park, followed by a sunset walk along the Hudson Riverwalk and a fun Halloween themed Tavern for dinner after. There are many activities that take place in the area during October. Here are a few.

Immortalized in Washington Irving’s famous tale, The Legend of Sleepy Hollow, this quaint village is located 25 miles north of New York City along the eastern shore of the Hudson River.

Halloween kicks into high gear during October when there are street fairs, hayrides, and ghost tours. A tour of the Old Dutch Church, founded in 1685, and the adjacent Sleepy Hollow Cemetery, which includes Irving’s gravesite, is a must-do.

In “The Legend of Sleepy Hollow,” the local tales surrounding the activity of the Headless Horseman seem to imply that the crossing of this bridge carries him from the land of the dead to that of the living – and back again – as he departs the burial ground of the Old Dutch Church and returns each morning before sunrise. At the high point of Irving’s Legend, Ichabod Crane, while fleeing from the Horseman, rides for the bridge in the hope of crossing a magic line of safety, a point where the Horseman’s powers dissolve. You can walk around the 90 acres free during the day or join a walking tour- they even offer nighttime lantern tours.  Visit here.

Rockefeller State Park is a short drive away and has 45 miles of scenic carriage roads to walk on, is dog friendly (on leash), rivers, numerous stone bridges, and has huge oak, tulip, poplar, maple, and beech trees. We saw cows (a private meadow runs adjacent), a woodpecker and numerous other birds. We ended the day watching the beautiful sunset along the Hudson. The Riverwalk Park is very nice located in nearby Tarrytown.

So even if you aren’t up on your literary classics, there’s plenty to do here and in nearby Tarrytown. The leaves will be peaking soon and the views of the Hudson River are gorgeous. Visit for information and upcoming events. Afterwards, we recommend Horsefeathers, an adorable tavern reasonably priced and decked out in Halloween decor in nearby Tarrytown. We’ve also been told by friends that the Horseman burger at JP Doyle’s is legendary- we will have to try this on another trip.

It’s a short train ride on the Metro North from NYC and a quick ride from Long Island. Happy Haunting Halloween lovers.



  • Roni Jenkins

    Roni Jenkins is a founding partner in The Three Tomatoes. She shares her social media and digital marketing savvy with the 3Ts. She is a Mom of three children, is actively involved in several non-profit organization, including the National MS Society and loves to run in the mud. She is inspired by her Mom and other women who have paved the way for working moms like her to be able to balance work and life. She is co-author (with her Mom) of two humorous book of quips, “Martini Wisdom,” and "More Martini Wisdom.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.