Who’s afraid of the headless horseman? Historic Sleepy Hollow, as well as surrounding Tarrytown and Croton-on-Hudson are the perfect destination for families this fall. Explore the Hudson Valley with your children as you take in the history and lore of the place that sparked the story of Ichabod Crane. Let kids enjoy some of the country’s most legendary Halloween celebrations!

This two hour walking tour takes you through the most essential (and spooky!) parts of downtown Sleepy Hollow and Tarrytown. The tour, led by the historical society, blends tales of real history with famed legends of a ghostly nature. Wear comfortable shoes and dress warmly as you will be walking and October can be brisk. Many current residents claim that the past still lingers in these towns, in ways both certain and inexplicably eerie. Enjoy seeing the historical highlights of the area as talented and knowledgeable tour guides regale you with all manner of stories. You’ll benefit both from new knowledge and the excitement of a little well placed spookery.

Tour the Estate of the Man Behind The Headless Horseman When in Sleepy Hollow

Continue your historical journey through this charming area on the Hudson with a visit to Sunnyside, the estate of Washington Irving, the man who penned The Legend of Sleepy Hollow. The building itself is a beautiful sight to behold, comprised of a variety of architectural styles. The beautiful grounds serve as another important element to the experience, with a spooky stroll through the woods making a great compliment to the tour, and a perfect way to get in the mood for evening Halloween related fun. Inside the house you’’ll explore local history, learn about the author and behold a number of items related to the “Legend” and its penning. Saturdays and Sundays there are shadow puppet performances that provide an extra treat for children.

The brief drive north to get to Croton-on-Hudson will be well worth it for this exciting scene. In addition, the Hudson Valley is gorgeous this time of year and the family will enjoy the colorful changing leaves and the splendor of the river. This truly unique and impressive spectacle features over 5,000 hand carved pumpkins, all illuminated. The mood is further set by eerie music and professional lighting as you wander a set path through an 18th-century gothic riverside setting and witness such spectacles as the “Tunnel O’ Pumpkin Love,” a “Doomsday” grandfather clock and a massive pumpkin bonfire. Many haunted house classics like spiderwebs, monsters and spooky sounds exist along this journey, but in a less graphic way that should be more appropriate for younger children.

Interested in booking or planning a vacation to Sleepy Hollow right now? Check out some of the amazing offers currently available for airfare and hotels at Kayak, Orbitz and Priceline. Need to rent a car? Try Hertz for great rates. See more lodging options at Hotels.com and Hilton. Get started on your next trip today!