Things To Do In Tarrytown NY: Top 23 Most Unique Spots | Stanton House Inn

Main Street of Tarrytown, New York

Tarrytown, NY, is a charming town nestled on the eastern banks of the Hudson River. It’s famous in the literary and Hollywood worlds. It was the home of Washington Irving, the author of American classics like Rip Van Winkle and The Legend of Sleepy Hollow. The town boasts beautiful views of the Hudson River, historic districts with 19th and 20th-century architecture, and unique shops and eateries. As part of Westchester County, Tarrytown is just a train ride away from bustling New York City. Its business district is a vibrant blend of old brick buildings, coffee shops, and hardware stores that evoke simpler times. Victorian houses line the streets, leading down to the river.


Ready to explore the best things to do in Tarrytown, NY? Let’s get into it.

Quick hits

  • Explore Tarrytown, NY for a spooky history and unforgettable experiences!
  • Visit grand mansions, scenic parks & trails, art galleries and more.
  • Don’t miss out on nearby Sleepy Hollow’s legend of the Headless Horseman or Yonkers’ culture filled adventure!


Map of the best things to do in Tarrytown, New York, from the Music Hall to the Sleepy Hollow Lighthouse
Map design by Stanton House Inn

A Brief History of Tarrytown, New York

Old Dutch Church, now surrounded by the Sleepy Hollow Cemetery, final resting place of many famous locals

Tarrytown is a village steeped in Dutch heritage. Its rich history dates back to the Weckquaesgeek Native American tribe, who fished the Hudson River here. The Dutch settlers arrived in 1640 and incorporated the area in 1870. The exact location of the first house is a mystery.


There are three yarns spun about the christening of Tarrytown:


  • One credits the Dutch and their fondness for wheat, or tarwe, which they hauled over from the old country.


  • Another points to an English settler from Long Island, a chap named Tarry who decided to put down roots here.


  • Then there’s the tale spun by Mr Irving himself. He wrote of housewives convinced their husbands were prone to dawdling in the village tavern on market days – hence, they “tarried” in town.

Revolutionary Era

Major John André was a spy who got himself caught in Tarrytown. His capture laid bare the treachery of Benedict Arnold. Three local boys were the ones who nabbed him, found him with plans for West Point’s defenses tucked away in his boot. Nowadays, the place is marked by Patriots Park, a farmers’ market where locals barter for fresh produce.


The Headless Horseman Bridge over the Pocantico River

Washington Irving, the man who penned “The Legend of Sleepy Hollow”, wrote about Tarrytown in 1820. Irving first escaped to Tarrytown during a Yellow Fever outbreak in NYC. His work inspired many adaptations, including Disney’s “The Adventures of Ichabod and Mr. Toad” and Tim Burton’s “Sleepy Hollow”. Tarrytown and the eastern bank of the river was known as Millionaires’ Colony a century ago, a playground for industry tycoons who built their lavish estates on its rolling hills. Their numbers included John D. Rockefeller. His mansion, Kykuit, finished in 1906, became the site of labor protests in 1914, quelled by the police in violent clashes.

The Best Things to do in Tarrytown NY

Looking towards the river, with a historic home or two in the shot

While of course not as famous as its neighbor, Sleepy Hollow, NY, Tarrytown is the more appealing of the two old Dutch settlements, year-round. That is, in this writer’s opinion.


Yes, Sleepy Hollow explodes into a frenzy during the Halloween season. But I find myself heading towards Tarrytown throughout the year, not just when I’m looking for something closer than Salem, MA.


Lyndhurst Mansion

Lyndhurst Mansion

This Gothic Revival mansion stands tall and proud overlooking the river. A national historic landmark, its cornerstone was laid in 1838. It’s perched above the Hudson Valley, like an eagle on its aerie. And it was the playground of the likes of William Paulding, merchant George Merritt, and Jay Gould.


This grand estate sprawls across 67 acres, and connects to trails where the hardy can hike and bike to their heart’s content. Lyndhurst Mansion offers tours that take you through rooms that recreate a grand past, historic gardens, and plenty of exhibitions. For the adventurous, the grounds are open for exploration. Be on the lookout for the Rose Garden and the Rambles.


Lyndhurst Mansion is a part of the National Trust for Historic Preservation. And if you’re a fan of the supernatural, you’ll be delighted to know it was a filming location for the 1960s TV series Dark Shadows. The mansion boasts a 1894 bowling alley and a swimming pool — luxuries then, and now.


Washington Irving’s Sunnyside

A stop at Sunnyside, the historic homestead of Washington Irving, is of course a must. Once a humble two-room Dutch stone house, Irving took it upon himself to transform it into a whimsical abode. The finished structure is complete with Tudor clustered chimneys, stepped gables, Gothic windows, and a Spanish tower. The rooms remain as Irving left them, complete with the original furniture. And the gardens of Washington Irving’s Sunnyside – well, they are a testament to his green thumb. The man who gave the early United States the “The Legend of Sleepy Hollow” wasn’t just a wordsmith, he was an avid gardener too. Sunnyside was where Irving spent his formative years and drew inspiration for his spine-chilling tale. Visitors can delve into Irving’s past and his contribution to American literature. One of the more unique outdoor activities here is participating in a scavenger hunt based on “The Legend of Sleepy Hollow.” It’s a literary lover’s paradise, a visit inside the mind of one of America’s earliest native writers.


Parks in Tarrytown, New York

And speaking of green thumbs, there are plenty of public parks to explore throughout town, and further up in the hills. The less remote ones even offer free Wi fi.


This is New York, after all.

Scenic Hudson RiverWalk Park

Scenic Hudson RiverWalk Park is a sanctuary for the soul. It’s a tranquil promenade beside the historic Hudson River. This park gifts you with a grand panorama of the Hudson. A river that has been the lifeblood and the muse of Empire State artists for generations. It’s easy to see from here why this particular river had its own school of artists, actually. The park is a green oasis, boasting terraces and lawns, and an eco-corridor teeming with native flora. A part of the extensive 51-mile RiverWalk, it abuts Pierson Park. And the path offers more than a few idyllic vantage points to admire the architectural marvel that is the Governor Mario M. Cuomo Bridge. The park is where locals and visitors alike indulge in biking, fishing, picnicking, or simply meandering.


The park also passes one of the most modern constructions in Tarrytown. Hudson Harbor, a chic condominium complex, stands where an asphalt plant and a soy sauce factory once did.

Patriots Park

Andre Brook flowing through Patriot's Park

On the border between Tarrytown and Sleepy Hollow, along Broadway, is where you’ll find a charming four-acre park named Patriots Park. This park across from Sleepy Hollow High School is the stage for a farmers market from May through October. It also boasts a playground and basketball court. Throughout the year, the park becomes a hub for various events, including the much-anticipated annual Duck Derby. The most appealing part of this park is the stream that passes through the middle. The towns have built bridges over it over the years, creating a rather whimsical landscape.


The brook is named Andre Brook. The name was for Major John André, a British spy caught nearby in 1780.


For some reason, Tarrytown, New York, likes naming its brooks after local traitors. There’s another one named after a different local Revolutionary War traitor near Pierson Park.


Tarrytown Lakes Park

This 72-acre spread of land, dotted with two man-made lakes, has trails for walking and biking, and spots for kayaking. The lakes, named Lower Lake and Upper Lake, were once the lifeblood of the town, providing drinking water in the late 19th century. But as time passed, these lakes near NYC retired from active service in the 1990s. Today, they are a sanctuary for wildlife and a popular spot for outdoor activities.


Old Croton Aqueduct Trail

It seems as if much of the history of Westchester County revolves around water supplies. Either water to supply a local town, or to supply the massive and ever-thirsty New York City.


The Old Croton Aqueduct, constructed from 1837 to 1842, once served as the lifeline for New York City. It transported water over a distance of 40 miles from the Croton River to reservoirs in Manhattan à la Roman aqueducts. Except this one was covered on its long journey.


Today, the trail that follows the path of this historic aqueduct, designated a state park in 1968. It’s now a favorite among hikers, this one included. This Upstate NY hiking trail winds its way through a variety of scenic and historic locations, including:

  • Sleepy Hollow
  • The Rockefeller State Park Preserve
  • Lyndhurst
  • And a stretch of woods


Eventually concluding at Highland Avenue in the town of Ossining, New York.

Rockefeller State Park Preserve

Pathway by a rockwall in Rockefeller State Park Preserve, one of the most popular attractions near Tarrytown

Rockefeller State Park Preserve, in nearby Pocantico hills, sprawls across 1,770 acres of untamed beauty. The tapestry of former carriage paths turned trails stretch 45 miles, meandering through the former estate of John D. Rockefeller and his son. The park is popular for jogging, riding, and walking. This verdant paradise is a home for over 202 species of birds and a stopover for Monarch butterflies on their journey south. The land, first bought by William Rockefeller in 1886, later fell into the hands of John D. Rockefeller.


Today, the park, open all year round, houses a gallery that showcases the marriage of contemporary art and natural history. The trails radiate out from Swan Lake and into the varied terrain of this expansive park. You’ll pass farmland, forests, swamps, and maybe a sheep herd with a friendly yet watchful guard dog. The sides of the trail are great for berry picking from burdened raspberry vines in the late summer months.


Visitors can park their vehicles at the Rockefeller State Park Preserve parking lot. You can park for a day for $6 via the automated machines.


Governor Mario M. Cuomo Bridge

The Governor Mario M. Cuomo Bridge, which replaced the Tappan Zee Bridge, is a New York State landmark. The bridge stretches its steel bones from Tarrytown in Westchester County to Nyack, NY, in Rockland County. The longest bridge of its kind in the Empire State, it straddles one of the broadest expanses of the Hudson River. The bridge offers vistas of the river and the landscapes beyond. You can pause at six overlooks and public art stops punctuating the length of the footpath. The path along the highway is quite lovely, with visitor centers at both ends, free Wi-Fi, seating areas, and bike racks.


When night falls, the bridge dons a mantle of light, its structure pulsating with the colors of the rainbow, thanks to an array of LED fixtures. On special occasions, the bridge’s lights change color, echoing the mood of the event. Just like the Empire State Building in Manhattan, the bridge’s lights don a different hue with every holiday.


Sleepy Hollow Lighthouse

Sleepy Hollow Lighthouse, close to Tarrytown, NYDepending on which side of the town line you’re on, this point is also known as the Tarrytown Lighthouse. And if you’re on the river itself, it’s the Kingsland Point Lighthouse.


Heck, I don’t really know. The Tarrytown Lighthouse has a lot of names.


This five-story monolith offers a spectacle of the Hudson River and a peek into the lives of a dozen light keepers and their kin. First lit in 1883, the lighthhouse used to be half a mile out in the middle of the river. Landfill over the intervening centuries has brought it closer and closer to the shoreline. It was a guiding light until 1961, when the Tappan Zee Bridge rendered the lighthouse obsolete. Today, it opens its doors to curious souls, having celebrated its 100th lighting anniversary in 1983. It’s a favorite spot along the Scenic Hudson RiverWalk Park from Tarrytown to Sleepy Hollow.


While I’ve never seen it from a kayak, it is possible.


Main Street

Main Street at sunset

The Main Street of Tarrytown is a draw in and of itself. You’ll be forgiven for thinking you’ve stepped into a Norman Rockwell painting while you’re walking.


Though you’ll snap out of it once you recognized that the food scene is much improved compared to mid-1900s Americana.


It’s an antique lover’s dream, with New York antique shops like Pretty Funny Vintage and Belkind Bigi. It’s a place that’s managed to hold onto its charm, with a third of its houses standing since before 1939.


Tarrytown Music Hall

Main Street of Tarrytown, and the Music Hall in the foreground

An old dame that’s been around since 1885, the Tarrytown Music Hall is the oldest theatre in Westchester. As a seasoned host to the likes of Miles Davis, Tony Bennett, and Louis Armstrong, the theatre has hosted a fair share of big names and grand performances. Even the Rockefellers and Vanderbilts have graced the halls. With less than a thousand seats, it’s no Madison Square Garden, but that’s part of the charm. The music hall is a place for intimate performances, where the music is the star, not the venue. Rock, jazz, blues, country, R&B, comedy – it’s all performed here. The Music Hall even hosts dance and film screenings. For this writer, the appeal is the exterior – beautiful wooden carvings, gold and red accents, and ceilings that reach for the sky.


And if you’re one for spooky tales, get this: the Tarrytown Music Hall is said to have some phantom performers! Reports of lights flicking on after everyone’s left and mysterious melodies echoing in the empty wings make you wonder… Is it a glitch, or the ghost of a diva who just can’t give up the spotlight?


And yes, I find ghost stories fascinating. I wrote an entire article about haunted places in Connecticut, after all.


Art Galleries in Tarrytown, NY

Got an itch for the arts? Tarrytown is your salve. It hosts a smorgasbord of diverse and intriguing media. A few to explore include:

Pocantico Hills

Entrance to Kykuit: the Rockefeller Estate

Pocantico Hills is not actually part of Tarrytown. This rural hamlet is part of Mount Pleasant, New York. Tarrytown, meanwhile, is part of Greenburgh.


The more you know.


Also, the Rockefeller State Park Preserve is actually in Pleasantville. But writing guides to all these separate towns sounds exhausting, so one master one it is!


Anyway, Pocantico Hills is wonderfully bucolic. And as the former playground of the New York elite, there are some impressive spots to explore up here.

Stone Barns Center for Food and Agriculture

Sheep at Stone Barns Center for Food & Agriculture

Stone Barns Center for Food & Agriculture, overlooking Tarrytown, NY, is a gastronomic and agricultural extravaganza. The farm sits on a bluff overlooking the valley. And the fine dining cuisine served at Blue Hill at Stone Barns comes from the surrounding fields.


The eggs likely popped out of a farm chicken that morning. And the pork from pigs that spent their lives wallowing in mud paddocks in the forests.


And you can visit with all of it, including the vegetable and fruit fields.


I just know less about that side of it, having worked here temporarily as a livestock manager, ages ago.


From experience, a few of the bluffs have the most idyllic views of the church spires of Tarrytown, the river, and the western banks beyond. And a few of the trails of the Rockefeller State Park Preserve pass by the farm, if you don’t feel like popping for the entrance fee.


Or very expensive food at the restaurant, which I’ve never had the luck of enjoying.


The lack of funds is likely more the issue. Eating local doesn’t come cheap, with real estate the way it is around here.


Union Church of Pocantico Hills

The Union Church of Pocantico Hills was a divine creation from the mind of John D. Rockefeller Jr. in the year of 1921. This humble, one-story sanctuary, steeped in the neo-Gothic style, stands on a bedrock of fieldstone. The main draw to this country church is the ethereal works of Henri Matisse and Marc Chagall, masters of the stained glass canvas. You can tour the Union Church, but don’t even think about snapping a photo inside. In 2006, it earned its place on the National Register of Historic Places.


View of the river from Kykuit

Another impressive estate, this one of the Rockefeller family, is Kykuit. With 40 rooms filled to the brim with art and family heirlooms, its an impressive realization of John D Rockefeller Jr.’s vision. Maintained by the Historic Hudson Valley, Kykuit: the Rockefeller Estate remains a huge draw to the area. The private art galleries, housing the works of Warhol and Picasso, among others, are a sight to behold. The Historic Hudson Valley conducts tours of the house, gardens, and empty basement passages. It’s a pleasant pass through the labyrinth of art and history that is Kykuit.

Seasonal Events in Tarrytown, New York


Now, Tarrytown is a town that knows how to throw a party. And it doesn’t shy away from the changing seasons either. Take a peek at what’s on the menu:


  • The Great Jack O’Lantern Blaze, held at Van Cortlandt Manor in Croton-on-Hudson, NY. Imagine more than 7,000 jack o’ lanterns of all sorts of designs.


  • The Headless Horseman Ball



  • Fall Family Festival



Tarrytown is always buzzing, always humming. So don’t be a stranger, join the fun when you can!


Restaurants & Shopping in Tarrytown, New York

The Taco Project, one of the many restaurants in Tarrytown, NY

This place knows how to satisfy a hungry soul with a spread of eateries, boutiques, and shopping outlets. Kick off the day with a cup of joe at Coffee Labs. Or if you’re in the mood for something substantial, head to Mint for a gourmet breakfast.


The TaSH Farmers Market, a bustling affair held in the historic Patriots Park, is a must-visit for fresh produce and eavesdropping on lively conversation. Come lunchtime, you’ll be spoilt for choice:



  • Bistro12 for a mix of Italian and Portuguese cuisine




  • My Tokyo for sushi that melts in your mouth


The restaurant, Horsefeathers, opened in 1981 on North Broadway. It’s a solid family restaurant with a welcoming atmosphere, a throwback to an old tavern. It has a large menu and many beer options, with local beer canned except on holidays. But the holidays, especially Halloween, are special, with pumpkin and fall-flavored beers during the High Holy Days for Tarrytown and Sleepy Hollow. The wedges are an excellent choice for lunch or dinner.


As the day winds down, Sweetgrass Grill, Tarry Tavern, or The Cube Inn beckon with their Cuban cuisine.


This writer is especially partial to dinners at:



  • Lefteris, for Greek food, preferably outdoors in nice weather


Retail therapy is in abundance too. Ona, a charming gift shop and art gallery, is a treasure trove of handmade goods and personalized garments. A few more options here include:



  • Belkind Bigi antiques



  • Pretty Funny Vintage



Are just a few places where you can spend a dollar or two.

Hotels, Inns, & Places to Stay in Tarrytown, NY

Tarrytown is approximately a 20-minute car ride from Greenwich, CT, making it a perfect destination for a day trip in the Hudson Valley. If you’re planning to stay for the weekend, there are several Tarrytown hotels to consider, all are easy pet-friendly getaways near NYC:

Unique Hotels in Tarrytown, NY

Enjoy a luxury getaway at the Castle Hotel & Spa in Tarrytown. Overlooking the Hudson Valley, this regal fortress offers breathtaking views, 31 lavish rooms, an award-winning restaurant, and an inn spa.


The Tarrytown House Estate on the Hudson is a delightful retreat nestled among the Hudson Valley’s lush greenery. This property, with a history spanning over 165 years, recently underwent a comprehensive $15 million renovation. This transformation successfully marries the estate’s traditional charm with a fresh, contemporary twist.

Bed and breakfasts near Tarrytown, NY

If you’re looking for a bed and breakfast in Tarrytown, you’re out of luck.


But venture about 16 minutes away to Chappaqua, NY, to stay at Crabtree’s Kittle House Restaurant & Inn. This establishment, originally constructed as a carriage house in 1790, is renowned for its farm-to-table restaurant. It boasts an award-winning wine cellar, which was once the estate’s stables. After indulging in the culinary delights, you can retire to one of the twelve rooms at the inn for a peaceful night’s sleep.


And 20 minutes driving will get you to our Greenwich, CT, bed and breakfast, Stanton House Inn. This charming inn occupies a mid-1800s mansion in the heart of nearby Greenwich, Connecticut. Each of our 21 rooms is unique and elegantly charming, for a cozy and comfortable stay. Wake up to a delicious continental breakfast, and spend the day exploring the area before returning to the comfort of your room. Spoken from experience, our location is a fantastic one for exploring both Connecticut and the Hudson Valley.

Directions to Tarrytown, New York

Winter road driving to Sleepy Hollow and Tarrytown

Now that you’ve got a hankering to visit Tarrytown, This quaint little spot is just a hop, skip, and a jump from NYC.


You can hop on a train from Grand Central on the Hudson Line of Metro North. Tarrytown is one of the easiest train trips from NYC. It makes for easy day trips on Metro North.


If you’re more of a road warrior, you’ve got a 30-mile stretch of asphalt calling your name from Manhattan, or a 60-minute jaunt from Brooklyn.


Once you’re there, you’ll find everything’s in spitting distance. Sleepy Hollow, the Tarrytown and Philipse Manor train stations, they’re all close. But if you’re the sort who likes to roam, you might want to consider bringing your own wheels. Especially if you’re planning on heading up to Pocantico Hills.


More Towns & Cities to Explore Near Tarrytown, New York

Ready to explore beyond the quaint charm of Tarrytown? There’s a wealth of neighboring towns and cities in Westchester County and the lower Hudson Valley just waiting to be discovered.


Sleep Hollow, NY

Philipsburg Manor, one of the historic sites in Sleepy Hollow

Washington Irving’s story has made a better introduction to Sleepy Hollow than this writer ever could.


The northern neighbor of Tarrytown changed its named from “North Tarrytown” after the success of Irving’s writing.


Which, obviously, upgrade.


For a quick itinerary of things to do in Sleepy Hollow, NY, try:


Taking a walk down Philipsburg Manor, a farmhouse and estate that’s been frozen in time, a relic from the 18th century.


When October comes around, the village dons a cloak of spookiness, making it feel like a scene straight out of a Tim Burton movie. Starting from Beekman Avenue near Broadway, you can explore the downtown area anytime of the year. That said, it’s during Halloween that it truly comes alive. Or during the Sleepy Hollow Street Fair, when the whole road closes to automobile traffic.


Start your day with a bagel from Headless Bagel. And when lunch or dinner time comes around, Beekman Ale House serves up a mean meal in a setting as old as the pub itself. From there, head to historical gems like the Old Dutch Church, Sleepy Hollow Cemetery, or back to Phillipsburg Manor. And if you’re in the mood for a scenic stroll, the waterfront and the Sleepy Hollow Lighthouse are worth a visit.


Even if you’ve already seen the Tarrytown Lighthouse. You won’t miss multiple visits.


Yonkers, NY

A brief drive from Tarrytown takes you to the up-and-coming city of Yonkers, New York. Explore the fascinating history of Yonkers at the Philipse Manor Hall State Historic Site. Dive into the city’s arts scene at the Blue Door Art Center and the Hudson River Museum. And don’t forget to take a leisurely stroll through Untermyer Park, home of stunning river views and beautiful historic gardens.

Ossining, NY

Discover the natural splendor and significant landmarks of Ossining, another Hudson River town close to Tarrytown. Explore some picturesque locations and the best things to do in Ossining, NY:

  • Teatown Lake Reservation
  • Sunny Ridge Preserve
  • Sing Sing Kill Greenway
  • Kitchawan Preserve

And if you’re up for a real adventure, swing by Crawbuckie Park/Nature Preserve for woodland trails and river views.


Ossining, NY, is the perfect destination for nature enthusiasts and history buffs alike.

Croton-on-Hudson, NY

The scenic town of Croton-on-Hudson, NY, boasts a variety of attractions and events for guests to relish. Some of the highlights include:

  • Visiting the historic Van Cortlandt Manor
  • Marveling at the engineering feat of the New Croton Dam
  • Taking in the scenic beauty of Croton Landing Park and Croton Point Park


These are just a few of the many things to see and do in Croton-on-Hudson.


Don’t miss the Great Jack O’Lantern Blaze at Van Cortlandt Manor, a must-see seasonal event that will leave you spellbound.


Tarrytown, New York, is a true Hudson Valley destination. Even if you’re not into historic mansions or hiking, the food scene and river walk alone is worth poking around here on an afternoon. It may not be as famous as Sleepy Hollow, but it’s a great place to visit anytime of year, including the Halloween season.

Frequently Asked Questions

How do you spend a day in Tarrytown NY?

Spend your day in Tarrytown, NY marveling at the Phillipsburg Mill, admiring the Headless Horseman sculpture and exploring the Sleepy Hollow Cemetery before having lunch on Beekman Street. It’s a perfect day of sightseeing for any active walker!

Is Tarrytown NY worth visiting?

Tarrytown NY is an incredible and historic destination, full of Dutch settlement to explore all year round. Fall especially offers many activities related to the Sleepy Hollow folklore, making it a must-visit destination for all literature fans.

What is Tarrytown New York famous for?

Welcome to Tarrytown, New York – the home of America’s first recognized author, Washington Irving, and his residence Sunnyside, open for tours. Not to mention, one of the oldest operating theatres – the historic Music Hall. It’s a place full of history and entertainment!

Is Tarrytown the same as Sleepy Hollow?

Sleepy Hollow and Tarrytown are two separate villages in two separate towns, despite being next to each other. Sleepy Hollow is part of the town of Mount Pleasant, while Tarrytown is part of Greenburgh. Tarrytown tried to separate from Greenburgh in the late 20th century, but the town didn’t want to lose the tax revenue from the General Motors factory that used to be here. So the secession movement lost. There’s been no concerted effort to breakaway since.

Is Tarrytown NY expensive?

Tarrytown NY is quite expensive, with housing costs over 25% more than the national average.

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