Tarrytown / Sleepy Hollow NY
Tarrytown and Sleepy Hollow are not your typical suburbs. Just a short, scenic train ride from Grand Central, these two villages cover a combined ten square miles and are home to about 10,000 people each. It often seems as if everything—from your morning coffee on the walk to the train to the ice cream cone you’ll enjoy as you stroll the streets at dusk—has been crafted with care. With a thriving arts scene, a passion for live music, and innovative chefs serving up ingredients fresh from local farms, it feels like you just stumbled onto the Brooklyn of Westchester.
Walking past the vast array of storefronts, you’ll feel as if you are in the epicenter of Westchester’s rivertown culture. The Saturday farmers market isn’t just about the fresh fruits and vegetables, its also about a community coming together, to listen to live music on the lawn, watch chefs share their crafts, or collaborate on art projects with their children. It’s a place that harkens back to the artist communities of the 1960’s, with a focus on family that is harder to find nowadays. You’ll see hoardes of commuters making their way down the big hill on Main Street on their morning commte, stopping for an espresso at Coffee Labs or a dark roast at Muddy Waters. Further north, at the Philipse Manor train station that services Sleepy Hollow, residents walk from their homes to the waterfront, waiting to step on the train and make the picturesque journey south along the Hudson River to Manhattan.
Rivertowns Westchester County NY
Though Tarrytown and Sleepy Hollow, formerly know as North Tarrytown, are often throught of as regions of the same town, they are actually links to two other distict towns. Tarrytown is a hamlet within the of Greenburgh, which also encompasses Ardsley, Dobbs Ferry, Elmsford, Hastings-on-Hudson, Irvington, and Hartsdale. Sleepy Hollow is a village within the town of Mount Pleasant, which also encompasses Pleasantville, Valhalla, Hawthorne, Pocantico Hills, Thornwood, and part of Briarcliff Manor. Tarrytown and Sleepy Hollow are throwbacks to earlier eras in human history, when the most active societies sprung up around rivers. Head toward the water from the train and you’ll find fields where kids can play ball against the backdrop of the brand-new Mario Cuomo Bridge. In the spring and summer, you can sit almost beside those double spans enjoying a drink after work Sunset Cove or Bridgeview Tavern. There are parades, and fireworks, and memories that last a lifetime. These are places where the sidewalks are full of friendly faces, where people walk to shop and eat, and where the community gathers often, in celebration of shared holidays, or even just a sunny day, surrounded by art, music, and the steady flow of the Hudson.
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Tarrytown NY / Sleepy Hollow NY Commute Times
Schools in Tarrytown / Sleepy Hollowy NY
For the Kids
Tarrytown is a haven for kids. The local schools embody the school spirit of a small town, and the community rallies around local sports teams. For younger ones, Pierson Park and Barnhardt Park both have well-equipped playgrounds and fun splash pads for cooling off on a hot summer’s day. A NU Toy Store sells new and used toys and hosts local author events.
AMENITIES & RECREATION
The outdoor recreation scene in Tarrytown and Sleepy Hollow revolves around the river, as they have some of the most accessible riverfront in Westchester. Poking out into the Hudson River with the New York City skyline in the distance, Kingsland Point Park provides spectacular views of the Palisades across the river, and is the place for stunning sunsets. If being on the water is your style, you can always rent a kayak and head out on the river for a “zoomed-in” view. Alternatively, Pierson Park offers the chance to enjoy the Scenic Hudson Riverwalk or take a tour of the Tarrytown Lighthouse, a favorite of the young ones for decades. For those who live an active lifestyle, the Old Croton Aqueduct is among the best bike trails in Westchester, running all the way to the upstate reservoirs. And Rockefeller State Park is a full-on nature preserve, featuring 1,400 acres, 180 species of birds, and former carriage roads, converted to trails, that offer the tranquil views of Swan Lake and the Pocantico River.
Food & Drink
Tarrytown / Sleepy Hollow NY & Surrounding Area
Top 10 Restaurants
$ . Tacos
$ . Sandwiches
$$ . Barbeque
$$ . Indian
$ . Vegetarian
$$ . American (New)
$$ . Korean
$$ . Japanese
$$ . Coffee & Tea
Like the other rivertowns, Tarrytown and Sleepy Hollow are full of charming mom-and-pop shops. Located in a Victorian house, Pretty Funny Vintage offers everything from housewares to the jewelry of yesteryear. On Main Street, it’s one quaint shop after another, from the Village Soccer Shop, where locals show their team spirit with shirts from almost every country, to Shaylula Jewelry, a boutique that is more Soho than Westchester. For socially conscious take on fashion and home goods, visit Ona, which, in addition to supporting local artists, features fair trade clothing made by artisans in struggling communities around the globe.
ARTS & ENTERTAINMENT
While every small American town has a Main Street, few match the diversity of offerings you’ll find here. It starts at the top of the hill, where the legendary Tarrytown Music Hall has been providing locals with access to some of the biggest acts in music and entertainment since 1885. The intimate venue has hosted everyone from Miles Davis and Louis Armstrong to Grateful Dead cover bands like Dark Star Orchestra. On over 180 nights a year, you can find comedy, music, or political programming right in your backyard. Tarrytown features one of Westchester’s finest rosters of restaurants and bars, many with riverfront views. With everything from craft beer bars to taco shops, Tarrytown is a walkable small town where residents never run out of options.
“In the bosom of one of those spacious coves … of the Hudson … there lies a small market town … known by the name of Tarry Town.” So begins Washington Irving’s classic short story, “The Legend of Sleepy Hollow.” While the story of Ichabod Crane is easily the most famous piece of Tarrytown’s history, the village has had many historical moments. The town was also where Major John Andre was captured during the Revolutionary War, revaling Benedict Arnold’s plan to give away the fort at West Point. Tarrytown was once the province of some of wealthiest Americans in history. Most famous among them was John D. Rockefeller, whose expansive estate today operates largely as public recreation space, but tours of Kykuit and it’s luxurious gardens are still a can’t miss. The same is true of Lyndhurst, the former estate of railroad tycoon Jay Gould. The history of wealth goes back even farther, as a visit to Washington Irving’s Sunnyside or Phillipsburg Manor is like stepping back in time to the 18th century. Due to the recent Irving Nostalgia, in 1995 the name of the town of North Tarrytown’s was officially changed to Sleepy Hollow, the name the land was known as before the 19th century.
Tarrytown and Sleepy Hollow are the best Halloween destinations this side of Salem. The annual Tarrytown Halloween Parade features costumes, prizes and marching bands, or head to to Jay Ghoul’s House of Curiosities, where a tour of the gothic Lyndhurst mansion turns into a murder mystery to be solved by the guests. It’s fun for kids of all ages. The Horseman’s Hollow is one of Westchester’s best haunted houses and attracts visitors from all over. People come to tour Sleepy Hollow’s cemeteries and visit the gravestone of Washington Irving.