Just the name of this village alone evokes images of quiet autumn nights, a horse and buggy rambling down a dirt road, and colonial homes that have yet to change since the 18th century. While Sleepy Hollow is all of these things, it's also so much more, making it a great destination all year round.
Located in the quiet Tarrytown on the shore of the Hudson River, Sleepy Hollow is a village that's modest but not boring in the slightest. In the fall, it comes alive to celebrate its history, but it's a history that exists in every area of the town to this day. And the good news? Most, if not all of it, can be seen in one full weekend.
Where To Stay In Sleepy Hollow
The scenic hillsides of the Hudson Valley and quaint streets that run throughout this village lend themselves well to the type of accommodations one would expect in a place such as this. Whether it's a historic inn or a locale that's easy on the budget, the right lodging can be found for anyone wishing to spend a weekend exploring Sleepy Hollow.
Castle On The Hudson
This hotel - which resembles more of a castle, hence the name - has been built in the traditional Norman style and dates back to the early 20th century. Easily reached by two main highways that run through the Valley, Castle on the Hudson also provides stunning views over the Hudson River.
- Cost/night: Starting at $379
Courtyard By Marriot Tarrytown Westchester County
A more affordable option but still upscale, the Marriot is within close proximity to the Sleepy Hollow Gardens. It's also near several great restaurants and provides great airport access for those who might be flying rather than driving.
- Cost: Starting at $169/night
Doubletree By Hilton Hotel Tarrytown
An affordable, upscale option is the Doubletree, which is within a 15-minute walk of the historic Lyndhurst Mansion in Sleepy Hollow. It's also near the airport and is easily located off South Broadway, which is within a few minutes' walk of the Hudson River overlook. This hotel is also home to the Sleepy Hollow Hotel & Conference Center.
- Cost: Starting at $139/night
What To Do In Sleepy Hollow
Of course, no visit to Sleepy Hollow is complete without reading the legend that was inspired by it. In 1820, Washington Irving wrote The Legend of Sleepy Hollow, which has inspired several spin-off stories, TV shows, and movies in the centuries that followed. Today, it's easy to see how the Headless Horseman could come galloping through any number of its colonial cemeteries or down one of its wooded Tarrytown streets. There are plenty of things to do that aren't associated with the legend, as well - and these should be on everyone's list.
The Headless Horseman Sculpture & Bridge
Those familiar with the tale will know that one of the most memorable parts of it was when the Headless Horseman threw a pumpkin at the main character, Ichabod Crane. It took place on a bridge which is now the Headless Horseman Bridge, right outside of Sleepy Hollow Cemetary and the Old Dutch Reformed Church (founded in 1685, making it one of the oldest in the country).
While the bridge has been very modernized, it's still a historic location nevertheless - and both the cemetery and the church are worth taking a closer look at. The famed author himself, Washington Irving, as well as famed historical figures William Rockefeller and Andrew Carnegie, have found their final resting places in the Sleepy Hollow Cemetary. It's home to 90 acres of land, so there's plenty of walking to be had in one day's time.
The famed sculpture of the Headless Horseman can be found just outside of the Sleepy Hollow Cemetary, and it's a great tribute to a tale that helped define this small village. Not to mention, it's 18 feet tall - so there's practically no chance of one missing it.
Philipsburg Manor
Both Sleepy Hollow and the neighboring Tarrytown share the same early colonial history that dates back to the late 17th century, and Philipsburg Manor is part of that, as well. This manor sits on the banks of the Pocantico River and is right across from the Headless Horseman sculpture, so it's not hard to spot. The manor itself was built about a century after settlers arrived in 1750, and visitors can tour the grounds and the property.
While on tour, guests will learn about the area's milling history as well as the dark history of the enslaved individuals who worked on the manor. While not all the history surrounding the manor has been positive, many find that it's an important thing to learn from regarding early life in America. The manor is also mentioned in The Legend of Sleepy Hollow so for those checking off historical stops, this is definitely one of them.
Where To Eat In Sleepy Hollow
One of the best things about dining in Sleepy Hollow is the sheer variety of food that's available in such a small village. Between both Sleepy Hollow and Tarrytown, there are plenty of options that are bound to appeal to any visitor.
Tarry Tavern
A local favorite that includes local fare on the menu, with a traditional pub-style for many of its dishes.
- $-$$
Sweet Grass Grill
Another local favorite that showcases the finest of Hudson Valley foods in its farm-to-table menu.
- $$
Lefteris Gyro
A great option for greek food done right, with a traditional menu that's especially great for vegetarians. The food is fresh, flavorful, and abundant.
- $
Bridge View Tavern
For craft beer lovers, this tavern is the place to be. With a minimum of 15 beers on top at all times, the pub-style menu is the perfect accompaniment to any one of them.
- $$