Given that Ichabod Crane and the Headless Horseman is now deeply embedded in America’s Halloween traditions, you’d think Tarrytown and the adjacent Sleepy Hollow would make the ideal location for a chilly Autumn getaway. But it might be even better suited for a spring or summer getaway.
You’ll find yourself wanting to spend most of your time outdoors if you visit Tarrytown once the flowers start to bloom. It’s right on the Hudson River, which means springtime visitors can enjoy idyllic river views from almost all of Tarrytown’s pristine parks. There are ample opportunities to craft an outdoor adventure that suits your comfort level, from casual walks through gardens and public estate grounds to more challenging hikes at a nearby nature preserve.
Tarrytown is all about its historical legacy, which is deeply rooted in the history of America’s founders and leaders of industry. The Rockefeller Family Estate, Kykuit, is unfortunately closed at the moment, but there are many other historic houses in Tarrytown open to the public.
Visiting these historic places can transport you back in time to the 19th century and even further back to America’s founding while taking in imposing houses and magnificent grounds. For visitors who’re especially keen to immerse themselves in the history of Washington Irving’s impact on the area, colonial life, and the American Revolution, The Historical Society of Tarrytown and Sleepy Hollow offer walking tours that cover all these subjects.
One can’t-miss day trip is, of course, Sleepy Hollow. Just a five minute drive from Tarrytown, you’ll find historic walking trails and landmarks, real-life locations from Irving’s stories, and opportunities for more rigorous outdoor excursions.
Its location along the Hudson River means that Tarrytown specializes in fresh seafood, so when you sit down to dine expect fresh oysters, scallops, and clams among other marine delicacies. A romantic dinner on the Hudson River is a must if you’re traveling as a couple, otherwise groups of friends will find a welcome environment at a beer garden overlooking the Tappan Zee Bridge.
No matter what the vibe of your vacay is, everyone will find something to love about Tarrytown, from eclectic restaurants, to historical sites, to seemingly endless trail options for hiking and walking.
Here’s everything you need to do, see, and eat in Tarrytown, New York.
We hope you love the Tarrytown hotels we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
Photo: Alexander Friedman/Shutterstock
Sunnyside, Washington Irving Historic House: Washington Irving’s estate is open for tours from August 6 to September 12. The lush grounds offer pathways to wander and roam on your own, but there are also tour guides (in costume!) stationed at different points around the property to fill you in on the history of Irving’s life in Tarrytown and the many intricate aspects of colonial life and architecture.
Where: 3 W Sunnyside Lane, Irvington, NY 10533
Lyndhurst Mansion: Located on the banks of the Hudson River, Lyndhurst Mansion and the accompanying grounds are the perfect location for a romantic stroll. There are guided tours of the impressive houses available, but curious explorers might also be keen to seek out the rose garden, restored Civil War-era paths, and so-called viewing platforms, where you can gaze out at the river views among the trees. A Daily Grounds Pass is required before entering the estate, which you can purchase online before your arrival.
Where: 635 S Broadway, Tarrytown, NY 10591
Scenic Hudson Riverwalk Park: The grass terraces and lawns at the Scenic Hudson Riverwalk Park are a great spot to lounge on a sunny day, but it’s the waterfront walkway that will make you stop and stare at the view of the Hudson River and the Tappan Zee Bridge, especially if you plan a walk for just around sunset.
Where: 250 W Main St, Tarrytown, NY 10591
Photo: Evan El-Amin/Shutterstock
Kingsland Point Park: Eighteen acres of forested parks, playgrounds, and hiking trails make Kingsland Point Park a worthy visit if you’re the type who likes to spend their vacations outdoors. The biggest draw to this park, however, is that it offers a close up view of the historic Tarrytown Lighthouse, which has been in operation for about 78 years.
Where: Tarrytown Light-Kingsland Point Path, Sleepy Hollow, NY 10591
Rockefeller State Park Preserve: All 1,700 acres of this nature preserve were donated by the Rockefeller family. Bird watching and horseback riding are just a couple of the activities encouraged on the preserve, but visitors can simply explore pastoral countryside of upstate New York and the preserve’s bridges, streams, and colonial stong walls and rock outcroppings.
Where: Route 117, 1 mile east of Route 9, Sleepy Hollow, NY 10591
Photo: WanderRoamRove/Shutterstock
Sleepy Hollow Cemetery: Washington Irving, Andrew Carnegie, and William Rockefeller are all buried in this legendary cemetery – and you don’t need to wait until Halloween to see it for yourself. Visitors can tour the gravesites on one of Sleepy Hollow Cemetery’s official tours (it’s strictly forbidden for groups to wander the grounds alone, however). History buffs can take a day tour, but there are evening lantern tours and an even darker and spookier two hour tour that covers all the murderers and crminals who have passed through the region. One other landmark to check out while you’re there is the Headless Horseman Bridge – the original bridge that was the inspiration for a scene in Irving’s story has long since rotted away, but the cemetery bridge is the perfect backdrop for a spooky selfie.
Note that cemetary staff emphasize that all guests must behave respectfully of those that have been laid to rest there.
Where: 540 N Broadway, Sleepy Hollow, NY 10591
Old Croton Aqueduct Trail: Originally a corridor that supplied clean water to New York City, the Old Croton Aqueduct Trail runs from Croton-on-Hudson to Yonkers. Today, the trail passes straight through Tarrytown and Sleepy Hollow. Stroller friendly and usually peppered with local joggers, this easy trail is a fun way to take in village life and natural landscapes in both towns.
Where: Old Croton Aqueduct State Historic Park, 15 Walnut Street, Dobbs Ferry, NY 10522
RiverMarket Bar and Kitchen: Natural and sustainable ingredients are the highlight of this beloved Tarrytown restaurant. Like many restaurants in Tarrytown, the focus here is on fresh seafood, and it comes in many delectable forms here: clam chowder, lobster bisque, grilled oysters, tuna tartare, and much more.
Where: 127 W Main St, Tarrytown, NY 10591
Mint Premium Foods: This cafe focuses on Mediterranean and Italian dishes that lean toward decadent flavors, including grilled dates, truffle burrata, seafood risotto, and wagyu beef burgers.
Where: 19 Main St, Tarrytown, NY 10591
Half Moon: Located in Dobbs Ferry just 15 minutes outside of Tarrytown, Half Moon is directly on the bank of the Hudson River. The views, especially at sunset, are transfixing as the orange and pink light plays off the rippling water. You won’t be disappointed in the food either. Fresh oysters and ceviche accompany heartier mains like lamb, lobster, and duck.
Where: 1 High St, Dobbs Ferry, NY 10522
Coffee Labs Roasters Inc.: There’s always a line outside this coffee shop in the morning, which hints at its status as a local favorite. Certified by the The Green Restaurant Association, the coffee shop features specialities like frozen blended coffees, fruit smoothies, and CBD infused coffees.
Where: 7 Main St, Tarrytown, NY 10591
Bridge View Tavern: Besides craft beers on tap and an outdoor beer garden, the appeal of this relaxed tavern is its bird nest view of the many Tarrytown landmarks, including the Tappan Zee Bridge and the Tarrytown Lighthouse.
Where: 226 Beekman Ave, Sleepy Hollow, NY 10591
Tarrytown Estate on the Hudson: The center of this sprawling hotel (which is split into several buildings) is a stone mansion built in 1840. The grounds cover 26-acres and overlook the Hudson River Valley.
Where: 49 E Sunnyside Ln, Tarrytown, NY 10591
Castle Hotel and Spa: Described as a “Norman-style castle,” this luxury hotel is positioned at one of the highest points in the Hudson Valley and has spectacular views. The Equus restaurant, awarded Four Diamonds from AAA, is also on the property.
Where: 400 Benedict Ave, Tarrytown, NY 10591