Sleepy Hollow

Stretching from New York City up to Albany, the Hudson Valley is a charming region of New York State that promises breathtaking views of the Hudson River and a variety of historical landmarks to explore. The array of wineries, state parks, and antique shops gives the valley a classic Northeast feel, making it the perfect getaway to escape the city’s summertime chaos. As an added bonus, the farthest part of the Hudson Valley is only around a three-hour drive from New York City. Keep reading to discover which 10 Hudson Valley towns make the perfect summer vacation spots.

1. Sleepy Hollow

Sleepy Hollow in the Hudson Valley
Photo by Darren McGee, Courtesy of New York State Department of Economic Development

The village of Sleepy Hollow is a lively community despite its name. Located just 25 miles north of Manhattan, the village is well known for its Headless Horseman lore that was born from Washington Irving’s 1820 tale The Legend of Sleepy Hollow. Irving was inspired by the village’s quaint beauty when he visited a friend in Tarrytown, and his infamous story became the reason the village was renamed Sleepy Hollow in the nineties. 

Because of the village’s connection to Irving’s spooky legend, visitors can enjoy many activities catered to the legend, including guided tours of the cemetery mentioned in the book. Interested in diving deeper? Come back during October for access to the Old Dutch Church when Sleepy Hollow dedicates the entire month to all things Halloween. If you aren’t interested in the lore, however, Sleepy Hollow has many other treats to enjoy as well. The award-winning TaSH Farmer’s Market is located on the border of Sleepy Hollow and Tarrytown. Visitors can try out local cheeses, fresh produce, and artisan baked goods. Then, after you leave, head to Horan’s Landing for some kayaking or maybe a jazz concert. Check out the nearby Sleepy Hollow Lighthouse as you stroll down the scenic RiverWalk, and grab a bite at Hudson Anchor restaurant to finish off the day.