History and legend, both literary and otherwise, frequently intertwine in both Tarrytown and Sleepy Hollow, home to Gilded Age mansions and the Headless Horseman, where you’ll find remnants of New York’s long and storied past on every street or, if you dare venture into the cemetery, buried right under your feet. But what should you do and see if you make the trip to these Westchester destinations? 

TOUR THE AREA’S HISTORIC HOMES 

For the first 200 or so years of its existence, Tarrytown and Sleepy Hollow were quiet agrarian villages, where churches and farms and mills took up most of the land. But that all changed in the 19th century. The expanding railroad connected the towns with New York City, 25 miles south, and the Industrial Revolution brought factories north, as well as newly wealthy men looking for a place to live far from the urban bustle. The boom of mansions around Tarrytown earned it a new nickname: “Millionaire's Colony.” 

Among the many estates that now dot the landscape, two in particular stand out: Lyndhurst and Kykuit. The former was built in 1838 for New York City mayor William Paulding Jr., but its most famous tenant was the railroad magnate Jay Gould, who bought the Gothic Revival mansion in 1880 and lived there until his death in 1892. Bequeathed to the state upon the death of Gould’s youngest daughter in 1961, the 67-acre estate was reopened as a museum and historical site. Visitors now can tour the two main floors, which are decorated with Gilded Age-era furniture and art, as well as the kitchen and servant spaces in the basement and the bowling pavilion built in 1894 by Gould’s wife Helen. You can also walk the grounds, which were landscaped to resemble the estates of European royalty and have spectacular views of the Hudson River. Lyndhurst hosts regular events as well, including arts and crafts markets, concerts and plays, and holiday-themed parties; check out their calendar for more info.

Kykuit, meanwhile, served as the Rockefeller family home. Patriarch and oil tycoon John D. Rockefeller Sr. began buying up land in nearby Pocantico Hills in 1893, eventually amassing over 3,000 acres; Kykuit itself sits on the highest point in the area, with unobstructed views of the Hudson River and the New York City skyline. The mansion, built in 1913 in the Classical Revival style, is four stories tall and has 40 rooms, resembling a massive bank turned into a palatial estate. Much of the interior design was done by John D. Rockefeller Jr. and his wife, Abby; their son, future Governor of New York and Vice President Nelson, acquired and displayed most of the art in the house, consisting largely of abstract modern sculpture. A tour today will take you through the mansion, showcasing the art, furniture and decor, such as the family’s immense china collection, as well as the carefully manicured grounds and gardens.

The other noteworthy house in Tarrytown belongs to its favorite son: Washington Irving. Born and raised in New York City, Irving came to Tarrytown as a teenager and fell in love with its history, and particularly the local ghost stories that inspired “The Legend of Sleepy Hollow.” After spending nearly two decades living in England and making his reputation as a writer, he returned to Tarrytown in 1835 and bought a two-room stone farmhouse on the banks of the Hudson. Irving remodeled and expanded the house in a hodgepodge of styles: Tudor Revival, Gothic, even a Spanish tower. He also had the grounds landscaped, adding trees, a pond, and a stream with a small waterfall. Rechristened as Sunnyside, it would be his home until his death in 1859. Restored and opened to the public in 1947, Sunnyside is a museum dedicated to Irving, featuring his original furnishings and giving visitors a look at what life was like in the 1840s. 

CELEBRATE SPOOKY SEASON AT SLEEPY HOLLOW’S CEMETERY 

Though Sleepy Hollow can be visited and enjoyed year-round, the town naturally comes to life in October and at Halloween. Skeletons, witches, pumpkins, monsters and — especially — the Headless Horseman pop up everywhere: in storefronts, on banners downtown, at street corners and on sidewalks. But to feel the true spirit of the season no matter when you’re there, head to historic Sleepy Hollow Cemetery, home of the Headless Horseman, and wind your way through the tombstones.

Sleepy Hollow Cemetery is located behind the Old Dutch Reformed Church, built in 1699 by Frederick Philipse, a wealthy Dutch merchant who owned a huge tract of land called Philipse Manor that made up present-day Westchester. It’s the second-oldest extant church in New York State and an integral part of “The Legend of Sleepy Hollow,” but it's not actually part of Sleepy Hollow Cemetery. Instead, the church has its own two-acre burial yard with graves dating back to the early 18th century; some of the tombstones are even inscribed in Dutch. 

The much larger Sleepy Hollow Cemetery, covering 90 acres, is the final resting place of some of the country’s most famous figures, including industrialist and philanthropist Andrew Carnegie, William Rockefeller, labor leader Samuel Gompers, Walter Chrysler (namesake of both the car company and the Manhattan skyscraper), cosmetics maven Elizabeth Arden, real estate developer Leona Helmsley, and, most fittingly of all, Washington Irving. Also within the grounds is a replica of the wooden bridge over the Pocantico River that Ichabod Crane tried in vain to reach while being chased by the Headless Horseman. (The actual crossing that Irving was referencing is right outside the cemetery, noted by a sign nearby.) The cemetery makes for both a peaceful nature hike and a trip back in time, guaranteed to give you some chills whenever you visit. 

CATCH A SHOW AT TWO STORIED VENUES 

Who needs Broadway? Visitors to Tarrytown can enjoy live entertainment at two historic performing arts centers: the Tarrytown Music Hall, and Jazz Forum. The former has been on the scene since 1885, when wealthy chocolate manufacturer William L. Wallace funded the construction of a two-story theater on Main Street. Designed by the architects of Manhattan’s Grand Central Palace (which was demolished in 1911 to make way for Grand Central Terminal) and the Macy’s at Herald Square, the Tarrytown Music Hall could do it all, hosting operas, sporting events, horse shows, and balls. It was one of the first movie theaters in the country, screening silent films beginning in 1901, and in 1915 was the site of the Cotton Ball, a women’s suffrage rally. It even saw two presidents speak from its stage: Theodore Roosevelt and Woodrow Wilson.

Converted to a full-time movie theater in the 1930s, the Tarrytown Music Hall fell into disrepair over the decades and was closed in 1976, with demolition on the docket. But a local arts and culture non-profit bought the building and did substantial renovations to get it up and running once more. Today, the Music Hall holds the distinction of being Westchester’s oldest operating theater, and in an echo of its past, it’s much more than a venue. Along with live concerts and performances, the Music Hall holds film screenings, art exhibitions, ghost tours and a holiday market, and they offer music, dance and acting lessons for local youth.

Jazz Forum, meanwhile, is the only dedicated jazz club in Westchester County. Open since 2017, you’ll find live jazz there every weekend from some of the best artists in the genre. Aspiring musicians can even take part in Jazz Forum’s once-a-month jam sessions: $5 gets you in the door and on the stage with a professional trio. Jazz Forum also offers a summer concert series with outdoor performances in Tarrytown (including at Lyndhurst), Sleepy Hollow, Dobbs Ferry and Ossining, plus a music program for preschoolers and an ensemble for kids in grades 5-12. If you’re in the mood for a fun night out with good music and a meal, make sure to stop by Jazz Forum. 

MORE EXPLORING 

The longest bridge in New York State can be found right outside Tarrytown. The Governor Mario M. Cuomo Bridge — formerly and still unofficially known as the Tappan Zee Bridge — spans three miles across the Hudson River, connecting Westchester County on the east side with Rockland County on the west through the town of Nyack. The current span, which replaced the original bridge that was built in 1955 and demolished in 2017, is over three miles long and 120 feet above the water, and it boasts eight 500-foot-tall towers that light up every night. Most days, traffic on the bridge is heavy, but you don’t need a car to experience it, as it has a 3.6-mile-long pathway for pedestrians and bikes, with scenic overlooks along the way and visitor centers at each end. 

Speaking of long walks: hikers and bikers alike will love the Old Croton Aqueduct Trail, which covers 26 miles between the Bronx and the New Croton Dam and cuts through Sleepy Hollow and Tarrytown. You can pick up the trail at Lyndhurst, near Sunnyside, and by Sleepy Hollow Cemetery. The trail itself follows the path of the Croton Aqueduct, which supplied New York City with much-needed fresh water from 1842 until 1955 through one of the state’s biggest and most successful engineering projects. 

If you want to learn more about the early history of Tarrytown and Sleepy Hollow, stop by Philipsburg Manor, a former manor house, mill and farm owned by the family of Frederick Philipse. The property is now a museum restored to its 1750 appearance, teaching visitors about colonial era farming, the history of the local Native Americans, and slavery in pre-Revolutionary America. The lives of the two dozen slaves who lived and worked at Philipsburg Manor are the museum’s main focus, and their experiences make for a sobering and fascinating look at both colonial and Black history.

A few miles outside of Sleepy Hollow, just past Kykuit, sits the Union Church of Pocantico Hills, which was built in 1921 by John D. Rockefeller Jr., in concert with his family’s development of the nearby area. What makes it worth seeing are two stained glass pieces commissioned by the Rockefeller family: a rose window done by Henri Matisse in honor of John’s wife Abby upon her death in 1948; and a Good Samaritan window done by Marc Chagall in honor of John upon his death in 1960. Tours of the church are offered multiple times daily through Historic Hudson Valley. 

A LITTLE BIT OF HISTORY 

Thanks to Irving, Tarrytown’s and Sleepy Hollow’s places in American literary history are secure. But we’d be remiss if we didn’t mention Tarrytown’s connection to the Revolutionary War, as it was where British army officer Major John André was apprehended and hanged as a spy by American soldiers in 1780. The papers found on André helped expose the plot to sell West Point to the British, foiling the scheme and forever tying the name “Benedict Arnold” to treachery and treason. Tarrytown also gained notoriety as a stop on the Underground Railroad, with escaped slaves finding shelter at the Foster Memorial AME Zion Church on Wildey Street; the church itself was founded by an escaped slave in 1860 and is the oldest Black church in Westchester County. For more on the area’s rich history, visit The Historical Society of Sleepy Hollow and Tarrytown, which has tons of memorabilia and artifacts and offers guided tours of their collection. 

HOW TO GET THERE 

Less than an hour away from New York City, Tarrytown and Sleepy Hollow can be easily reached on Metro-North. Take the Hudson line to the Tarrytown Metro-North station, where you can see the Hudson River Explorers artwork by Tom Patti Design.

Alternatively, for some railroad history, take Metro-North one stop past Tarrytown to Philipse Manor. Its station was built in 1910 in a Tudorbethan style and is on the National Register of Historic Places, one of two Hudson line stations to earn that honor. The main station building was restored in the 1990s, and is now home to the Hudson Valley Writers Center, which regularly holds readings, workshops and open mic nights.