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Visit Legendary Sleepy Hollow, NY, This Fall

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“If ever I should wish for a retreat whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.”

It’s with these words that Washington Irving’s nameless narrator describes the now proverbial Westchester glen that sets the scene for his tale, “The Legend of Sleepy Hollow.”

I picked up a hardcover copy of the classic on a recent weekend trip to Sleepy Hollow, N.Y. Reading it again after experiencing the sights and places that likely inspired Irving, I found that the picture of a seemingly bewitched, sheltered and unchanging respite rings true.

Close enough to see the silhouette of the Manhattan skyline and beautifully flanked by the changing colors of the trees, yet far enough away to appreciate the slower pace of its charming downtown areas, historic properties and river views, Sleepy Hollow country is an ideal place to get into the spirit of fall and Halloween.

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Experience Fall in and Around Sleepy Hollow, N.Y.

Irving wrote “The Legend of Sleepy Hollow” while living in England, but it’s said that his Tarrytown memories influenced the portrayal of the starring village. At his Sunnyside estate, you’ll feel transported back in time as guides in 19th century costumes walk you through the restored rooms of Irving’s romantic, red-roofed cottage overlooking the Hudson River. Admission is by timed tours only, Thursdays through November 9 and weekends Mid-Nov. through mid-Dec.

If you’re dreaming of a Sleepy Hollow Halloween, Sunnyside hosts a dramatic retelling of “Irving’s Legend,” weekends in October. This is your chance to catch a glimpse of the Headless Horseman, so reserve tickets in advance. On select dates Sept. through Nov., there’s also Home of the ‘Legend,’ a ticketed event where visitors can see the house decorated for the season and enjoy some family-friendly fun.

Not far from Sunnyside is the village of Sleepy Hollow, which officially adopted its moniker in 1996. The Old Dutch Church and churchyard, described as the Headless Horseman’s headquarters in the story, are here. Sleepy Hollow Cemetery, while not the setting in the story (but easy to confuse), is where Washington Irving is buried.

Check out more scenic and historic graveyards in the Northeast.

A tunnel of illuminated pumpkins at the Great Jack O’ Lantern Blaze,
A tunnel of illuminated pumpkins at the Great Jack O’ Lantern Blaze, held annually at Van Cortlandt Manor in Croton-on-Hudson, N.Y. (Photo: Westchester County Tourism & Film)

More Fun Nearby

While you’re in the Tarrytown area, you’ve got to see the Gothic Revival castle at Lyndhurst decked out in its autumnal best. Fall mansion tours are offered throughout the season. Or go at night to get acquainted with the mansion’s spooky side at Lyndhurst After Dark.

One of the area’s most popular events, the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson, runs through the end of November. The walk-through attraction features incredible themed displays made from more than 7,000 hand-carved illuminated pumpkins.

For even more Northeast fall fun, check out Your AAA Fall Fest.

Featured image: Master storyteller Jonathan Kruk offers a dramatic performance of Washington Irving’s classic tale, “The Legend of Sleepy Hollow.” (Courtesy of Visit Westchester)


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