10+ Legendary Things To Do In Sleepy Hollow NY For Couples

Sleepy Hollow, New York is the stuff of legends where history, folklore, and modern-day adventure converge. Often associated with Washington Irving’s haunting tale of the Headless Horseman, this picturesque village offers more than just spooks and fall traditions.

Whether your sweetie is a history buff looking to unravel the rich tapestry of America’s early days, an outdoor enthusiast eager to explore the scenic Hudson River, or someone who simply enjoys a unique cultural experience, here are thrilling things to do in Sleepy Hollow NY for the ultimate weekend getaway near New York City.

Looking for more romantic getaways? Check out our list of Romantic Getaways In New York State.

Where Is Sleepy Hollow NY?

Sleepy Hollow is located in Westchester County, New York, along the east bank of the Hudson River. It’s about 25 miles north of Manhattan, making it easily accessible for both day trips and longer stays from New York City. From Grand Central, a Metro-North train gets you to Sleepy Hollow in under an hour.

The village is part of the town of Mount Pleasant and shares its southern border with the village of Tarrytown. Originally established as North Tarrytown, the village officially adopted the Sleepy Hollow name in 1996.

Welcome to Sleepy Hollow sign

The Sleepy Hollow Legend

Washington Irving wrote The Legend of Sleepy Hollow in 1819 while living abroad, but you can tell where his heart lay from the details that opened the story:

In the bosom of one of those spacious coves which indent the eastern shore of the Hudson, at that broad expansion of the river denominated by the ancient Dutch navigators the Tappaan Zee, there lies a small market town known by the name of Tarry Town

thus setting the stage for the strange sights and events to which poor Ichabod Crane would be subject. Irving continued,

…the place still under the sway of some witching power that holds a spell over the minds of good people, given to all kinds of marvelous beliefs and who frequently see strange sights and hear music and voices in the air.

Irving was so enamored of the Hudson River, in fact, that he decided to retire along its banks in the mid-1800s. Irving’s home, Sunnyside, is open to the public, as are a number of historic restorations, including John D. Rockefeller’s estate, Kykuit, and other historic sites of significance.

Fun Things To Do In Sleepy Hollow NY (& Nearby)

Headless Horseman Sculpture

PHOTO OPP: Headless Horseman Statue

The Village of Sleepy Hollow fully embraced its Headless Horseman legend, even erecting an 18′ high rusty metal sculpture in 2006 that is now one of the area’s most popular roadside attractions.

Located in front of a gas station along Route 9, there is limited parking, but it’s just across the street from the Visitor Center where you can also pick up tickets to Ghost Tours, historic home tours, dramatic performances such as Horseman’s Hollow, Irving’s Legend, The Unsilent Picture, and highly anticipated Halloween events such as The Great Jack O’ Lantern Blaze.

WALKING TOUR: Sleepy Hollow Cemetery – Sleepy Hollow NY

Pay your respects to Washington Irving and the locals who inspired his writings at The Sleepy Hollow Cemetery (where Irving is buried) and adjacent Old Dutch Church and Old Dutch Burying Grounds, which was originally constructed by Frederick Philipse for his employees.

Daytime and evening guided tours are available, for a fee, by prior registration. Walk-ins are welcome (Monday-Friday, 8:30-4:30) and free maps point out the most famous (or infamous) of residents, among them: Washington Irving, Andrew Carnegie, William Rockefeller, Elizabeth Arden, and Harry and Leona Helmsley.

Self Guided Tour

Pick up free maps from the chapel building just inside the main gate, and then choose your direction. It’s possible to circumnavigate both cemeteries in one big walking loop, or if pressed for time, drive to one end or the other to explore those areas.

If you go straight in you can walk across the Headless Horseman Bridge.

Couple leans over Headless Horseman Bridge at Sleepy Hollow Cemetery

Alternatively, a right turn takes you toward the South Gate and the oldest parts of the cemetery. Along the way, you pass the Civil War Monument on the exterior perimeter.

Cannon balls and flags at Civil War Monument - Sleepy Hollow Cemetery - Sleepy Hollow NY

Just a little further on, detour into the interior of the cemetery to see the gated area holding America’s first best-selling writer, Washington Irving.

Entrance to Washington Irving gravesite at Sleepy Hollow Cemetery in Sleepy Hollow NY

Peer over the gate to see Washington Irving’s headstone.

Washington Irving's headstone in Sleepy Hollow Cemetery.

But you might need a telephoto lens to get a good look at the gravestone.

Washington Irving Gravestone at Sleepy Hollow Cemetery

If you turn around and squint a little you can almost imagine how this fairytale land might have had a “witching effect” on the Rip Van Winkle author.

Couple on romantic getaway peer into landscape at Revolutionary War Monument - Sleepy Hollow Cemetery
The Revolutionary War Monument in Sleepy Hollow Cemetery faces out on Pocantico River, a 9-mile-long tributary of the Hudson River in New York’s Westchester County.

Down a small hill, between the Revolutionary War Monument and the South Gate, lies New York’s oldest standing church, the Old Dutch Church and Burying Ground. The Dutch Reform Church is a National Historic Landmark, and also a functioning house of worship.

Old Dutch Church - Sleepy Hollow, NY

Surrounding the church are some of the oldest gravestones and some of the earliest examples of American folk art.

Early American folk art and gravestone - Sleepy Hollow Cemetery

Sleepy Hollow Cemetery covers 85 acres, not including the Old Dutch Church & Burying Ground section. Interesting possibilities for meandering walking tours abound.

Philipsburg Manor, Tarrytown NY

TOUR: Philipsburg Manor – Sleepy Hollow NY

In 1693, William and Mary of England granted 52,000 acres of land along the Hudson to a carpenter named Frederick Philipse – who built his Manor home in Tarrytown and set up a milling/farming/trading complex managed for the most part by industrious and intelligent slaves.

Little did Mr. Philipse know that a hundred years down the line, his property would become famous as the stomping ground for Washington Irving’s Headless Horseman and that the Old Dutch Church, which he constructed for his workers, would be the final resting place for Irving and the many local residents who inspired his stories.

The manor and its grounds have been restored to give visitors a feel for 18th-century farm life – and does an admirable job – letting kids thrash then winnow wheat and turn a heavy grinding mill among many other interactive exhibits. Open May through early November.

Sleepy Hollow LIghthouse

GO: Sleepy Hollow River Walk

The Sleepy Hollow River Walk runs along the Hudson River, offering panoramic views of the Cuomo Bridge, Manhattan, and the Palisades. As you traverse this waterfront trail, you’ll encounter landmarks like the historic Sleepy Hollow Lighthouse and the vibrant Riverfront Community Mural.

Situated at the site of the former General Motors Assembly Plant, the walkway ends by the lighthouse. However, future plans will extend the path to offer a 51-mile shoreline pathway in Westchester County.

Cuomo Bridge Path

GO: Cuomo Bridge Path

The Cuomo Bridge Path offers a unique way to experience the Hudson River, providing pedestrians and cyclists with a dedicated lane to traverse the Governor Mario M. Cuomo Bridge. On the western side of the Hudson, there’s a bunch of yummy restaurants and cool shops in Nyack, artist Edward Hopper’s hometown. (Find a curated list of recommendations in our Nyack NY travel guide.)

Spanning approximately 3.6 miles, the path features six overlooks, each designed as a resting spot where visitors can take in panoramic views of the Hudson Valley and Manhattan skyline. Equipped with LED lighting, seating areas, and interpretive displays, the Cuomo Bridge Path is a marvel of modern engineering blended with thoughtful design.

Sunnyside Home of Washington Irving Sleepy Hollow NY

TOUR: Sunnyside, Washington Irving’s Home – Irvington NY

With its ivy-wreathed portico and gingerbread-hued exterior, “The Snuggery,” as Irving called it, puts one in mind of a fairy-tale cottage. Costumed docents lead you through the home and property where Irving lived out the last years of his life. Washington Irving, named after our nation’s first president, was born in New York City and lived in England as a young man.

He was the first American writer “celebrity,” and the first to make a living completely from his books. Built in 1835 in a mishmash of European styles – Dutch, Roman, English, Mediterranean – with thick vines added to create an antiquated appearance, Sunnyside was the only home that the author, then in his mid-40s, ever owned. The public ate it up. Called “America’s Cottage” by the press, the house became almost as famous as Irving was.

The “Snuggery”

Front door to Sunnyside Washington Irving Sleepy Hollow NY

I’ve made secret plans to move into Sunnyside ever since I first set eyes on it as a young girl. I could toil happily in the cozy study (filled with Irving’s original furniture and leather-bound books) just off the front door before retiring to the plush green parlor where French doors open up to a river-view patio.

From here, a perfect Hudson vista is marred by utility poles and train tracks laid in 1849. Until then, Irving and his friends would travel to and from New York City by boat and disembark at his small private dock. As one of the country’s first NIMBY’s, Irving fought the railroad and lost.

He did manage, however, to eek one concession out of the deal – his own private rail station, which gave Washington Irving the distinction of being the first suburban commuter into New York City – just 1-½ hours away back then (vs. almost 3 hours by boat). Irving lived with trains passing a few dozen yards from his home for ten years until his death in 1859.

Kykuit, Tarrytown NY

TOUR: Kykuit: The Rockefeller Family Estate – Tarrytown NY

As the estate that housed four generations of Rockefellers, Kykuit is a prime example of a beloved family home generously transferred over to the public. John D., founder of Standard Oil Co., built Kykuit in 1906, and throughout the years, it’s interesting to note how each generation put its own stamp on the home and gardens.

John D. Sr, a strict Baptist, did not see the need for a grand ballroom or staircase, as this was to be his family’s country home and not a place to entertain. His portrait, done by famous artist John Singer Sargent, hangs in the dining room.

Kykuit view from front door, Tarrytown NY

Unlike his grandfather, Nelson Rockefeller, Governor of NY and Vice President of the United States under Gerald Ford, loved to entertain, and added a significant amount to his family’s art collection.

Kykuit as Art Museum

He created an ersatz Museum of Modern Art in Kykuit’s basement and filled it with Calders, Motherwells, and 30 Picassos, including 11 rare Picasso tapestries. (Nelson’s father, John D Jr., had grown up with the medieval Unicorn Tapestries, which he had donated to the Cloisters. Jr. loved the medium so much, he called on Picasso himself to create the pieces).

Torso by Maillol, Kykuit, Tarrytown NY

Nelson installed switches in the living room that would illuminate and rotate a statue of Aphrodite in the inner garden – seen through the room’s picture window.

Kykuit’s gardens were designed by William Welles Bosworth – the acclaimed landscape architect of the day. Enriched by 19th and 20th-century sculpture from artists like Henri Moore, Degas, and Rodin, the grounds of the 87-acre estate are terraced – one leads to another to another – and what appears to be a vast romantic landscape is really laddered acreage that blocks the view of downtown Tarrytown below.

This illusion of grandeur was Bosworth’s calling card and is what most visitors come to see. Open May through early November.

Exterior of Union Church of Pocantico HIlls in Sleepy Hollow NY

TOUR: Union Church of Pocantico Hills – Tarrytown

You don’t have to go to France (Notre Dame Cathedral of Reims) or Israel (Hadassah Hospital in Jerusalem) to see stained glass windows designed by Marc Chagall. All you have to do is drive to this small 75-family church a few miles from Tarrytown NY, pay $7 for a tour, and walk in the door. Commissioned by John D. Rockefeller Jr. in the 1940s, the nine windows (four on each side of the sanctuary, and a larger one on the rear wall) were installed, with some degree of controversy, in the ’60s.

“Not everyone was onboard with modern art in a church,” says a docent. Chagall, a French Jew who came to the United States in the 1940s to escape the Nazis, created emotional portraits of six Hebrew prophets – Joel, Isaiah, Elijah, Jeremiah, Ezekiel, and Daniel – though I have to admit that the Prophet Elijah looks very Christ-like.

The Rose Window over the altar was created by another notable artist, Henri Matisse. Plan on at least 30 minutes here and take the tour. It’s a wonder more people don’t know about this place. Be aware, that this is an active Church so Church events take precedence.

GO: Rockefeller State Park Preserve

Covering over 1,700 acres, Rockefeller State Park Preserve is crisscrossed by a network of well-maintained carriage trails designed by John D. Rockefeller. Ideal for hiking, running, bird-watching, and even horseback riding, the park provides a biodiverse habitat that includes wetlands, forests, and meadows.

Tarrytown Music Hall

SHOW/MUSIC: Tarrytown Music Hall – Tarrytown NY

The best of the best play here, be they musicians – Squeeze, Loretta Lynn, Marshall Tucker Band – or comedians – Jackie Mason just to name a few. Right on Main Street, within steps of great restaurants, this venue has been growing in popularity over the last few years.

Lyndhurst, Tarrytown NY

TOUR: Lyndhurst – Tarrytown NY

Occupied by empire-builder, Jay Gould in the late 1800s, this Gothic Revival mansion is separated from the Hudson by a forest laced with hiking trails and provides great views of the brand spankin’ new Cuomo Bridge (aka the Tappan Zee.)


TOUR: Armour–Stiner Octagon House – Irvington NY

First built in 1872 in the form of a Roman temple, The Octagon House has been expanded over the years. In 1978, preservation architect, Joseph Pell Lombardi, purchased the home and restored the grounds and home to its original appearance. Though the home is full of Victorian-era treasures, visiting the interior of the dome itself is worth the price of entry. Though in private hands, the Octagon House, just a few miles from Sleepy Hollow, is open to the public periodically for small-group tours. 

Seafood Tower at Hudson Farmer & The Fish
Seafood Tower at Hudson Farmer & The Fish

Sleepy Hollow NY Restaurants

SEAFOOD: Hudson Farmer & The Fish – Sleepy Hollow NY

The Hudson Farmer and the Fish offers a delightful blend of rustic charm and culinary sophistication. Specializing in farm-to-table cuisine, with a particular focus on seafood, guests enjoy fresh oysters from the raw bar, inventive seasonal dishes, and an impressive wine selection. Reclaimed wood, maritime accents, and floor-to-ceiling windows with breathtaking views of the Hudson River invite you to linger over a leisurely date. And because it’s right next to the Riverwalk, plan on a romantic stroll before or after.

Candlesticks burn down at Goosefeather Restaurant Tarrytown

EAT: Goosefeather – Tarrytown

Celebrity Chef, Dale Talde, knows his way around drunken noodles and other Cantonese dishes – as evidenced by the excellent Hudson-Valley-Asian-fusion cuisine at his restaurant, Goosefeather. Situated in the King Mansion of the Tarrytown House Estate in Tarrytown NY, Goosefeather brings a bit of cool flash and whimsy to this Hudson River town.

Why Chinese? “Have you seen how many Italian places and bistros there are here?” says Talde, who made his name on Top Chef and other cooking contest shows before opening his seminal restaurant, Talde, in Brooklyn in 2012. “There was nothing like this kind of unconventional, upscale Chinese – it was all take-out.”

The 1840 King Mansion served as a private home, and then the boutique inn within Tarrytown House before Talde got a hold of it and turned four rooms on the main floor into an Art Nouveau-Antebellum-esque restaurant space.

Miro murals on dining room ceilings at Goosefeather Tarrytown NY

Dine beneath Miro-art ceilings in the glow of dozens of candles – dripping together like wax sandcastles – and the meal becomes an experience to savor. And, savor I did. The popular dim sum, Dry Aged Beef Pot Stickers, dipped in spicy horseradish mustard, was out of this world.

And, I couldn’t get enough of one signature – Black Pepper Beef: succulent cubes of crunchy-tender meat lacquered with a hoisin/basil sauce. Other dishes also hit a high mark for my vegan husband: Wild Mushroom Slippery Noodle, and the vegetarian version of the ordinarily surf and turf Supreme Rice.

As for desserts, one Italian staple, Tiramisu, has infiltrated the menu. Talde, of course, made it his own – with Green Tea mocha, Passion Fruit mascarpone and diced sweet citrus. I’m not generally a Tiramisu fan, but I lapped this version up as I’d never be able to get it again. But of course I will. The next time I visit – with friends.

Couple strolling garden paths at Blue Hill at Stone Barns

EAT: Blue Hill at Stone Barns – Pocantico Hills

“An exhibit, a classroom, a laboratory, and a garden,” Blue Hill at Stone Barns in Pocantico Hills incorporates a working farm and acclaimed restaurant (RSVP necessary) where “fast food” means from farm or garden to plate with no travel time.

Casual dining is available at the Blue Hill Cafeteria, plan on dressing up a bit (no shorts!) for the Blue Hill at Stone Barns experience.

EAT: Lefteris Greek Restaurant – Tarrytown

Shout “OPA” at the popular Lefteris Greek Restaurant; where the salad dressing is so popular, that they bottle it for purchase.

Sleepy Hollow NY Hotels

Tarrytown House Estate main building Tarrytown NY

STAY: The Tarrytown House Estate – Tarrytown

Established as a conference center, the Tarrytown House Estate, which encompasses hotel and meeting rooms in several buildings, is fast becoming a chic lodging option for leisure travelers, too, in no small part due to Goosefeather. (See Best Restaurants above).

Across Route 9 and a few hundred yards up the road from Sunnyside (Washington Irving’s home), rooms in the main building of this beautifully landscaped complex have been updated in a handsome grey palette.

Miro capped room at King Mansion Tarrytown House Estate NY
Like Goosefeather, the rooms in the King Mansion at Tarrytown House Estate are embellished with Miro art, but in black and white.

For something more romantic, ask for one of the ten Miro-art embellished chambers upstairs from Goosefeather Restaurant in the King House, an 1840’s white mansion within the complex.

Twelve-foot ceilings, hardwood floors, four-poster beds, and renovated bathrooms add to the deluxe experience. Book one of the coveted four corner rooms, which are a bit larger and allow balcony access through French doors. From your perch, you get unobstructed views of the Mario Cuomo Bridge and Manhattan in the distance.

Castle Hotel and Spa, Tarrytown NY

STAY: Castle Hotel and Spa

If you wish to splurge on overnight accommodations, revel in the refined luxury of The Castle Hotel and Spa. With its stone tower and granite walls offset by cozy brocade furniture and dark wood beams, you half expect King Arthur to saunter through the door.

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  • Malerie Yolen-Cohen and Sandra Foyt

    Travel experts Malerie Yolen-Cohen and Sandra Foyt share all-in-one destination guides for the best romantic getaways. Although they generally publish independent articles, this is their collection of collaborative posts. Malerie’s focus and specialty is the Northeastern USA, and she is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. Originally from the Caribbean, but based in New York's Capital Region for over twenty years, Sandra specializes in warm-climate destinations.

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