Visit Sleepy Hollow
Sleepy Hollow is a perfect escape from the bustling city of New York, located just 50 minutes by train or 40 minutes by car from Manhattan. This charming town, steeped in legends, has its roots in the narrative of Washington Irving.
In 1820, Irving wrote the famous story of “The Legend of Sleepy Hollow” or “The Legend of the Headless Horseman”, set in the picturesque valley of Sleepy Hollow in Tarry Town. The plot revolves around the specter of a Hessian soldier whose head was hit by a cannonball during a battle in the American Revolutionary War. At night, this ghost rides in search of his lost head.
The influence of this legend on the town, originally called North Tarrytown, was so profound that it culminated in the official change of its name in 1996.
It is possible to visit Sleepy Hollow all year round, although it is especially attractive in October and during the Halloween celebration. This month, the town comes to life with the legend of the Headless Horseman, transforming into a setting full of pumpkins, haunted mansions and horror stories that add a special touch to the experience.
Sleepy Hollow and Tarrytown are contiguous towns, located next to each other, making it easy to explore on foot in a single day. Sleepy Hollow stands out as home to the most Halloween-related attractions, while Tarrytown offers a wide variety of shops and restaurants.
Both towns, for the most part, have a residential character and are characterized by their charming areas with impressive houses and mansions. The proximity between these two places allows visitors to enjoy both the experiences related to the Halloween festival and the commercial and gastronomic offer in the same tour.
During the fall, especially beginning in mid-October, both Sleepy Hollow and Tarrytown, along with the entire Hudson Valley, are dressed in a palette of dazzling reds and golds. This season offers a stunning visual spectacle, making it an exceptional time to explore these charming towns. However, the beauty of the region is present all year round, providing visitors with an enchanting experience whenever they choose to explore it.
Below is a list of those must-see places in the Town of the Headless Horseman that are worth visiting:
1. Old Dutch Church
Old Dutch Church is the oldest church still standing in New York State. Built in 1685 by the owners of Philipsburg Manor, this historic church sits across the street from the estate that now serves as an interactive museum. Adjacent to the church is the old cemetery known as Old Dutch Burying Ground, where some graves of Dutch settlers rest that date from before the construction of the chapel. This cemetery adds an extra touch of history and authenticity to the environment.
2. Sleepy Hollow Cemetery
Very close to the church is another of the most visited places: the Sleepy Hollow Cemetery.
It is recommended to take a guided tour, if possible, to discover the stories of some of the most illustrious residents, such as Washington Irving, Andrew Carnegie or William Rockefeller. For those who prefer to explore the cemetery independently, maps can be purchased at the entrance.
3. Philipsburg Manor
The towns of Tarrytown and Sleepy Hollow have their origins around Philipsburg Manor, an 18th-century farm and mill that has been meticulously restored to offer an authentic glimpse into the daily lives of settlers and slaves during colonial times.
Even for those who do not wish to visit the interior, the place has a cafe and a souvenir shop that are open all year round. As an additional fact, the back has views of the mill that are simply beautiful. Philipsburg Manor thus offers an enriching experience for both those interested in history and those seeking to enjoy a picturesque setting.
4. Washington Irving House
South of Sleepy Hollow in Tarrytown is Washington Irving’s home, known as Sunnyside, which offers a stunning view of the Hudson River. This historic residence, declared a heritage site, allows visitors to explore its rooms and discover furniture, books and other objects that belonged to the first internationally recognized American writer. To visit, it is possible to reserve through the Historic Hudson Valley organization’s website.
5. Rockefeller Estate: Kykuit
Visitors should not miss the opportunity to explore Kykuit, the majestic mansion that was the epicenter of the Rockefeller empire for four generations.
This tour is a worthwhile experience that requires careful planning, since the visits are guided and have a limited number of places. Without a doubt, the significant influence of the Rockefeller family in the construction of modern New York that we all admire stands out, highlighting its historical and cultural importance.
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