Halloween in the Historic Hudson Valley: Haunted Houses, the Headless Horseman and More

When a dear friend of mine moved away from New York City to take a job in Poughkeepsie, NY, I worried that she would never find anything to do "up there" in the Hudson Valley. However, after a few visits, I discovered that the Hudson Valley has a lot to offer, especially around Halloween. Hudson Valley hosts an amazing array of Halloween activities, sure to frighten even the bravest of souls.

Sleepy Hollow, NY
Anyone who loves Halloween has probably heard of "The Legend of Sleepy Hollow," an eerie 19^th century tale by Scottish-American author Washington Irving. What many people may not know is that Sleepy Hollow is a real place, located in the Historic Hudson Valley, about 30 miles north of midtown Manhattan. Metro North trains stop in Sleepy Hollow, making it a great option for those without cars. Fans of the Sleepy Hollow legend will enjoy going to the Old Dutch Church and Burying Ground, where Irving's story takes place. The original Headless Horseman bridge has been destroyed, but there is another bridge just downstream which is a perfect substitute. Sleepy Hollow is also home to Philipsburg Manor, a historic farming and milling center. Philipsburg Manor offers educational tours most of the year, but at Halloween, the manor is transformed for Legend Weekend. During the day, there are Halloween-themed activities for kids, including pumpkin carving, magic shows and ghost stories. At night, ghouls, ghosts and other characters from area folklore come to life and haunt the grounds. There's even a special appearance by the area's most famous apparition, the Headless Horseman. It's truly a great place to get into the Halloween spirit.

Croton-on-Hudson, NY
Just 10 miles north of Sleepy Hollow, Croton-on-Hudson is home to Van Cortlandt Manor, another historic manor house. Like Philipsburg Manor, Van Cortlandt Manor offers tours and colonial demonstrations most of the year. However, at Halloween, it hosts the Great Jack O'Lantern Blaze, a spooky spectacle featuring over 4,000 hand-carved jack o'lanterns arranged along a walk through the manor grounds. It's truly breathtaking. Legend Weekend and the Great Jack O'Lantern Blaze can be visited on the same night for a full evening of Halloween thrills.

Ulster Park, NY
If you're willing to travel a little farther from the city, Headless Horseman Hayrides and Haunted Houses in Ulster Park is a great option. Located 80 miles north of Sleepy Hollow, Ulster Park is not accessible by Metro North, but those with cars will find plenty of Halloween fun to make the trip worthwhile. This attraction features a corn maze, a hayride, and 3 different haunted houses for a full 3-hour fright tour - even Gilligan and the Skipper would be scared!. Though the event is "family-oriented," children under 5 are not allowed in the evening, and it is not recommended for children under 8. This part of the Hudson Valley is full of U-Pick apple orchards, pumpkin patches and beautiful fall foliage, so there are plenty of fall-themed ways spend your day before your Halloween night of fright.

My friend moved away from Poughkeepsie last year, and I will definitely miss her annual Halloween party, which was always a high point of my Halloween trip to the Historic Hudson Valley. However, I will continue to make the trip, to enjoy all of the fabulous, frightening and freaky Halloween attractions that are just minutes away from my home in New York City. Come visit the Historic Hudson Valley this Halloween - the Headless Horseman is waiting!