Sleepy Hollow Hudson valley ny
Oct 17, 2018

Day Trip to Sleepy Hollow

By Joanne Colella

Sleepy Hollow Hudson valley ny

It is clear to see that the quaint Hudson Valley town of Sleepy Hollow – the setting of the classic Headless Horseman tale by author Washington Irving – has embraced its storied reputation, encouraging guests to visit “where the legend lives.” Now is the perfect time to make a day trip to this charming and historic venue, where colorful autumn landscapes and spine-tingling Halloween celebrations beckon.

Located just 20 miles outside of New York City and bordering Tarrytown, NY – about a 90-minute drive from central New Jersey – Sleepy Hollow is easily accessible. During the fall season, it offers a fabulous array of haunted hayrides, Gothic mansions, farmers’ markets, pumpkin patches, historic sites, wooded hikes, festivals, parades, live entertainment, and more – many of them free.

Headless Horseman aficionados will want to see some favorite haunts from the story, including landmarks such as the site of the Van Tassel homestead where schoolmaster Ichabod Crane began his flight from the horseman. Another is the spot where British spy John Andre was captured and exposed the treasonous American general Benedict Arnold, as well as the 17th-century Philipsburg Manor millpond, the Old Dutch Church, a rock formation known as Raven Rock, and the true “sleepy hollow” located in a secluded valley stream that meanders through the area. Unfortunately, Ichabod Crane’s schoolhouse and the famed bridge where he met up with the scary specter now exist only in memory.

Sleepy Hollow Cemetery Tours offer the opportunity to stroll among monuments and mausoleums to visit the final resting places of such notable names as Elizabeth Arden, Brooke Astor, Andrew Carnegie, Walter Chrysler, William Rockefeller, and – of course – Washington Irving. Dating back to 1849, the 90-acre Sleepy Hollow Cemetery is home to almost 45,000 souls. You can walk or drive the grounds on your own or try a guided tour.

In October and early November, you may enjoy the popular day or evening tours, such as The Original Knickerbocker: Washington Irving & The Legend of Sleepy Hollow; The Classic Lantern Tour; Murder and Mayhem Evening Lantern Tours; or The Good, The Bad, and The Unusual. Times, details, and pricing vary, and advance reservations are needed.

On a few October dates, the cemetery also hosts literary events, with ghost stories by Washington Irving, works from Edgar Allan Poe, and – for kids ages 7 to 12 – a local storyteller’s presentation of spine-tingling cemetery tales. The cemetery is open to visitors Monday through Friday from 8 am to 4:30 pm, and Saturday and Sunday from 8:30 am to 4:30 pm. It is located at 540 North Broadway, with a small parking lot inside the south gate, adjacent to the Old Dutch Church.

For those not too timid to be truly terrified, the annual Horseman’s Hollow provides 15 nights of ominous entertainment on the grounds of the 17th-century Dutch colony of Philipsburg Manor. Visitors who dare to walk along the haunted trail will view scary scenes of a town driven mad by the Headless Horseman, with a host of creatures lurking in the shadows.

Be forewarned that this event is not suitable for adults who are claustrophobic, have heart or respiratory conditions, are prone to seizures, or have other chronic health conditions. Philipsburg Manor is located at 381 North Broadway. Scheduled for weekends through October, tickets are $20 each ($25 on Saturdays) and can be reserved online at or call 914-366-6900.

Another not-to-be-missed Halloween event – the biggest in the area – is the hugely popular Great Jack O’Lantern Blaze, taking place this year through Saturday, Nov. 24. More than 7,000 uniquely hand-carved pumpkins will illuminate the darkness amid the riverside setting of the 18th century Van Cortlandt Manor. Most nights sell out in advance and times vary; get your tickets early at 914-366-6900. The price is $22 for adults and $16 for kids age 3 to 17 ($27 and $20, respectively, on Fridays and Saturdays). Van Cortlandt Manor is located at 500 South Riverside Ave., Croton-on-Hudson, NY.

Halloween may be the theme for a visit to Sleepy Hollow now, but there is plenty more to see and do in the area at every time of year. Prepare for a frightfully fun day trip and explore all the details at