Seniors Stop In Sleepy Hollow

Legend_of_Sleepy_Hollow_U.S._StampYes, Senior Citizens, there really is a Sleepy Hollow. The village “Where the Legend Lives” is located on the east bank of the Hudson River, about 30 miles north of New York City. To the south of Sleepy Hollow is the village of Tarrytown. The population of the village runs just under 10,000.

Incorporated as North Tarrytown in the late 19th century, in 1996 the village officially adopted the traditional name, Sleepy Hollow. “The Legend of Sleepy Hollow”, a short story about the local area and its infamous specter, the Headless Horseman, was written by Washington Irving, who lived in Tarrytown and is buried in Sleepy Hollow Cemetery.

Owing to this story, as well as the village’s roots in American history and folklore, Sleepy Hollow is considered by some to be one of the “most haunted places in the world.” Seniors, let’s go explore Sleepy Hollow and see what is there for attractions and fun things to see and do.


Unfortunately, the bridge where Ichabod Crane was unseated by a pumpkin, is the most popular destination in Sleepy Hollow that doesn’t exist—at least, not in the form and location in which it appeared in Washington Irving’s short story, first published in 1820.

Seniors Enjoy Everything Haunted

Historic Hudson Valley notes that taking the tale of The Legend of Sleepy Hollow to its darkest extremes, Horseman’s Hollow returns to the village for 15 evenings of highly entertaining haunted mayhem.


Philipsburg Manor transforms into a terrifying landscape ruled by the undead, the evil, and the insane. Senior visitors can walk a haunted trail, stumbling upon scary scenes of a town driven mad by the Headless Horseman. The Hollow’s unfortunate inhabitants are all too ready to keep visitors from ever leaving. So if your heartbeat can’t take a little scare to two, beware:)

How about taking a good old fashioned Haunted Hayride? After the ride plan to take in Sleepy Hollow Cemetery,  it’s on the Register of national Historic Places and the final resting place of legendary author Washington Irving. You can experience many activities including haunted attractions and Halloween festivals like the incredible pumpkin Blaze and scary Horseman’s Hollow.

Seniors Find Rockefeller Estate and Philipsburg Manor


For me, I’d want to visit Kykuit, known also as the John D. Rockefeller Estate. Old Dutch Church of Sleepy Hollow and Old Dutch Burying Ground, founded around 1685, is the church and churchyard that appear in Washington Irving’s short story. It is often confused with the adjacent but separate Sleepy Hollow Cemetery.

Philipsburg Manor is another “must see” site on North Broadway. It is a 17th-century historic site that tells the story of slavery in the colonial north. Senior visitors can enjoy a plethora of outdoor adventures with parks, forests, rivers, lakes, streams and trails along one of the most scenic stretches of the Hudson River.

Check out all the history, scenery and hospitality in Sleepy Hollow that is as legendary as the tale itself. -jeb

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