Sleepy Hollow New York and the surrounding area practically scream Halloween unlike any other part of the country. Experience the legend of the headless horseman with kids and take the family through a town that does fall holidays like no other. Children will love the fun, creative and spooky atmosphere while parents will enjoy the fact that they are also learning and enjoying the outdoors on this idyllic fall day.
Please note that this is not an itinerary submitted by an actual family. This day was planned by one of our travel experts as a recommendation for a family of children with ages 4 through late teens, based on knowledge of the city. Factors such as time, cost and distance have been considered to make this a great day to get a sense of the city and keep the
children and teens interested and engaged.
Address: Cemetery Office at 540 North Broadway, Sleepy Hollow, NY
Hours (Fall 2014): Two-hour guided walking tours, Saturdays and Sundays, October 5-6, 12-13, 19-20, 26-27; 2 PM. November 1,2, 8 and 9 at 2 PM. Off season (or during the week), self guided tours can be taken during the hours of 8:30 AM to 4:30 PM daily.
Admission: Two-hour tours $19.99. Advanced reservations required.
While exploring a cemetery may not sound like a fun family activity, Sleepy Hollow’s is one of the most beautiful and historic in the country. It’s impressive list of famous interments is further enhanced by a beautiful selection of mausoleums, 18th century headstones and impressive statuary all set on a gorgeous hill. The special tours are fantastic during the day, or you can choose to guide yourself for free with a map available at the cemetery office or online. This second option is not quite the same as the famous Halloween-time guided tours, but is cheaper and available year round. Another consideration in choosing how to visit is that the guided tour spans about two hours, covers over a mile of ground and traverses unpaved roads, hills and stairs so may be beyond the patience and abilities of the youngest children. If you are on the other end of the spectrum and want to excite older kids with something extra fun and spooky, look into the themed evening tours.
Address: 635 South Broadway, Tarrytown NY 10591
Hours: You can wander the grounds at any time, however consult the website to make sure a ticketed event doesn’t coincide which may prevent you from accessing certain areas.
Getting There: 15 minute drive South on US-9 to get to Lyndhurst, minor driving to see other sites.
Admission: Free of Charge
Enjoy literally hundreds of unique scarecrows “invading” the grounds of the gothic mansion Lyndhurst in Tarrytown. These unique creations range from scary to funny and everything in between. Wander at your own pace and take them in, perhaps gathering some inspiration to go home and create your own house-haunting denizen as a family with some newspaper and old clothes. Besides the gaggle at the castle, see more scarecrows spread out around town with a large grouping in Patriots Park, lone soldiers lashed to lamp posts along Broadway and Main Street, as well as a giant Tim Burton inspired scarecrow at the intersection of Beekman Avenue and Route 9. Finally, anyone in the know can tell you that the scariest ones of all are hiding outside Horseman’s Hollow…if you dare to explore.
Address: Old Dutch Church, Sleepy Hollow, NY. Park at Philipsburg Manor lot. NOTE: No Parking On Site, Park across the street at Philipsburg Manor, 381 North Broadway, Sleepy Hollow, NY.
Hours (Fall 204): Four performances each evening on the hour, beginning at 6 pm. October 4-5, 10-12, 17-19, 24-26, 31. November 1.
Getting There: 9 minutes North on US-9 from Lyndhurst
Admission: Adults, $16; Children under 18, $12. Must Purchase in Advance.
No Sleepy Hollow Halloween experience would be complete without the famous “Legend of Sleepy Hollow” story by Washington Irving. The best way to experience it is in a dramatic telling, set to spooky organ music and delivered by master storyteller Jonathan Kruk. Experience the classic tale, complete with the Headless Horseman, Ichabod Crane, Brom Bones, and Katrina Van Tassel. An added treat is the impressive setting of the Old Dutch Church which both adds to the spooky ambiance and provides a further dose of history.