Plunder Boys

Pirates drop anchor along the Hudson.

Forget Johnny Depp. In fact, forget the Caribbean. The area’s true swashbucklers are going to be at Philipsburg Manor for Pirates of the Hudson: The Siege of Sleepy Hollow from July 2 to July 4. (Because nothing says patriotism like a little piracy.)

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    Pirates, after all, have been known to sail the Hudson—and cause consternation for Frederick Philipse, the Lord of the Manor. “The Philipse family businesses involved, among other things, trading on the high seas, and piracy was a huge issue,” says Rob Schweitzer, spokesperson for Historic Hudson Valley. “Legend holds that Frederick Philipse and Captain Kidd were, indeed, friends, and Kidd would land at Kingsland Point to meet with Philipse and trade with him, likely from his prizes as a legal privateer. When Kidd was named a pirate in 1698, Kidd and Philipse’s friendship would have greatly hurt Philipse’s name, and it may or may not have been used by then-Governor of New York Lord Richard Bellomont in kicking Philipse off the Governor’s Executive Council.”

    Oh, those dastardly pirates. But if you can’t beat ’em, join ’em, which is why the manor is home to a family-friendly, pirate- and gypsy-themed festival. Though it’s produced by the same creative team that put together the Horseman’s Hollow last Halloween, Pirates of the Hudson is more of a free-flowing celebration than the Horseman’s linear haunted-house path. One area will be home to the “Thieves’ Market,” where visitors can try and pick up some booty (while avoiding scurvy pick-pockets). There will be a “Museum of Oddities” to display things like the bones of a Japanese sea serpent. The “Grace O’Malley Pirate Training Center” will put your little ones through their paces in pirate-training activities, and there will also be a real, live shipwreck for them to crawl through. The famished can sample grog from Captain Lawrence, as well as seaworthy snacks such as “Pirate Fingers” (pigs in a blanket) and “Pirate Teeth Salad” (featuring corn and peppers) from Tastefully Yours.

    “That was the most important thing—to create something that appealed across all demographics,” says Lance Hallowell, the event’s creative director. “In the Grace O’Malley Pirate Training Center, for example, they teach the kids how to be pirates. But there is also a blacksmith right there who is going to be telling people about the nautical uses of boarding axes and grappling hooks that pirates used to board other boats quickly.”

    “You can learn to talk like a pirate,” says Schweitzer. “You can learn to swordfight like a pirate. On the surface, it seems like those activities are just for kids, but I think adults will wind up liking that, too.”

    Roving throughout all the areas will be a band of performing pirates, gypsy sword dancers, and other assorted scalawags who interact with the landlubber visitors. “We were very diligent that they were all pirate-themed,” says Hallowell. “In one of the areas, we have Riverrat Hornswoggle. He is basically a shyster character that just pulled up onto the docks and is looking to make a quick buck—but he’s also a magician. Everything is very steeped in piracy to make sure it’s a complete and full experience.” (Watch out for the “Buccaneer’s Brawl” that takes place every hour.)

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    For the Horseman’s Hollow, Hallowell and his team looked to Washington Irving—who lived right up the road at Sunnyside in Irvington—for spooky inspiration. This time, Irving’s writing turned to be helpful again. “We didn’t have to look that far,” Hallowell says. “It was easy to go back to Washington Irving with Tales of a Traveller,” which tells of Captain Kidd’s exploits along the Hudson River.

    Irving wasn’t the only one to give us some local pirate lore, though—and some of it might give hope to local treasure-hunters. “Landings along the Hudson, including Cold Spring, Verplank Point, Montrose Point, and Half Moon Bay, are all named as possible places Kidd came ashore to bury his treasure chests,” Schweitzer says. “Many legends even make reference to one of his treasure ships, under command of his quartermaster, hitting a tempest at Stony Point and sinking to the bottom of the Hudson!”

    But before you dig out your shovels, you’re going to need to spend some time with some pirates. Pirates of the Hudson: The Siege of Sleepy Hollow takes place from 3 to 8 pm July 2, 3, and 4. Admission is by timed ticket only. For more information, call (914) 631-8200 or visit




Scurvy pirates roam among the crowd.

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