Hudson Valley, NY
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Hudson Valley, NY

The Headless Horseman rides again...

Destination Guide

It's the weekend. Your children can: A) blast monsters on their computers all day or B) tour historic sites in upstate New York with Mom and Dad. If it happens to be Halloween, and the destination is the ghostly land of Ichabod Crane and the Headless Horseman, you may have more cooperative company in the car than you expected.

Just 26 miles from Manhattan, Sleepy Hollow, in lower Hudson Valley, is like a scary movie set come alive -- especially during October's annual Legend Weekend. This is, after all, where you'll find the once fictional -- and now real -- town made famous by author Washington Irving in The Legend of Sleepy Hollow. (The hamlet of North Tarrytown officially changed its name to Sleepy Hollow in 1996.) The short story, of course, features one very ghoulish "Headless Horseman."

During Legend Weekend, ghouls, witches, and even Headless Horseman clones visit Philipsburg Manor; and spooky events take place at Sunnyside, Irving's home. In fact, Sleepy Hollow is one spooky place to take the kids at Halloween.

Headless Attractions

Huguenot Historial
Society, copyright
G. Steve Jordan

Just walking the hills where this caped equestrian allegedly rode can be more thrilling for your young ones than killing off e-monsters. (But make sure they know the story first.) Pick a foggy day (or night) for maximum effect, and get Dad to make low moaning noises as you tour these top spots:

  • Philipsburg Manor. At the end of October, spookiness reaches its height at this 300-year-old working farm with a grist mill, cited in Irving's short story. The buildings are candle-lit at night, and creepy characters are everywhere. What's more, the Headless Horseman makes an appearance on horseback. The farmer's ball is re-created (after that party, the Horseman chased Ichabod Crane). And ghosts and witches fill the landscape. During the day, the activities are a bit tamer, with jack 'o lantern carving sessions and storytelling. Other times of year, Philipsburg is still a good place to take the kids. They'll love watching the water-powered grist mill (fresh ground corn flour is for sale) and touring the 18th-century barn, where they can get up close and personal with Nip and Tuck, a pair of 2,000-pound oxen.
  • Sunnyside. Come see where America's first superstar author lived. Besides Sleepy Hollow, Irving also wrote Rip Van Winkle -- and fans have been scoping out his riverfront cottage since the 1800s. During Legend Weekend, your wide-eyed little one can listen to spooky tales told during walks in the woods (reservations are required), make scarecrows, watch a Legend of Sleepy Hollow puppet show, or listen to a reading of Irving's stories.
  • The Old Dutch Church and Burying Ground. Washington Irving's hapless Ichabod Crane was headed to this 17th century church when he ran into the "Horseman." (The encounter did not go well for Crane.) Tour New York's oldest house of worship (still actively used), or poke around the 350-year-old graveyard. Legend has it there may still be ghosts lurking here.

Headless Paraphernalia

Freer Church, copyright
G. Steve Jordan

Before moving on to the grown-up attractions, make an important stop at one of the museum shops or gift stores in Tarrytown. You'll find all sorts of Headless Horseman sweaters, flags, coffee mugs, and keychains, which are good bribe material. Logo items including T-shirts are a hot souvenir. So are copies of Irving's books and colonial-themed games.

Landmarks not to Miss

Tarrytown is loaded with National Historic Landmarks, including very old homes and living museums, which offer family activities throughout the year (except January and February). They include:

  • Van Cortlandt Manor in Croton-On-Hudson. This 18th-century manor house decorated with period furnishings includes a tenant farmer's house and 18th-century tavern. Kids will particularly enjoy demonstrations of 18th-century American life offered in the tenant house, including cooking, spinning and weaving. There are also demonstrations of blacksmithing and brickmaking on the grounds.
  • Kykuit. The Rockefeller Estate is great for parents, but not children under 12 (too boring for them). The six-story mansion was home to four generations of Rockefellers. Inside there's an art collection and fancy furniture. The grounds offer views of the Hudson, formal gardens, and fountains, as well as 20th-century sculpture collected by Governor Nelson A. Rockefeller (including works by Picasso, Moore, and Calder). In the barn are more than 20 classic cars from three generations of Rockefellers, from a 1918 Crane Simplex to Nelson Rockefeller's 1959 Chrysler Limo with his Governor license plates.


Type of trip: Historic, educational, scenic drive

Best for ages: 6 and up

Length of trip: Day trip or weekend getaway.

Distance: New York (26 miles); Hartford (92 miles); Scranton, PA (128 miles)

Best time to go: September/October, for the Hudson Heritage Festival (including Legend Weekend) and Children's Book Festival; April, for Washington Irving's birthday celebration at Sunnyside (with puppet shows and storytelling), and Memorial Day weekend, for Animals and Acrobats at Van Cortlandt Manor.

Weather: 65/49 degrees in October, 61/43 in April, 71/53 in May.

Squirm factor: Some, to a lot.

If You Go...

Huguenot Historial
Society, copyright
G. Steve Jordan

Legend Weekend. At Philipsburg Manor and Sunnyside (see below).

Philipsburg Manor Route 9 in Sleepy Hollow Phone: 914-631-3992

Sunnyside Off Route 9 in Tarrytown Phone: 914-591-8763

The Old Dutch Church and Burying Ground Route 9, Sleepy Hollow Phone: 914-631-1123

Van Cortlandt Manor Off Route 9, nine miles north of Sleepy Hollow in Croton-On-Hudson Phone: 914-271-8981

Kykuit Off Route 9 in Pocantico Hills Phone: 914-631-9491 Not recommended for children under 12. NOTE: Tours depart from Philipsburg Manor. Purchase tickets at the Manor or online.

More Information

  • Historic Hudson Valley
    Phone: (914) 631-8200
  • Westchester Convention & Visitor's Bureau
    Phone: (800) 833-9282


Inside Scoop

Favorite local spots:

  • Rockwood Hall
    Rockefeller State Park Preserve
    Route 117 East off Route 9 in Sleepy Hollow
    Phone: 914-631-1470.
    This picnic spot with great views is located near the foundations of a Rockefeller home, overlooking the Hudson. Plan on a five-minute walk from the closest parking or one-hour hike from the Visitor's Center.
  • Horsefeathers
    94 North Broadway in Tarrytown
    Phone: 914-631-6606
    When the stomach rumbles, head to this literary-themed pub restaurant, where you'll find home cooking including burgers, salads, sandwiches, steaks, pastas, and chili, and a children's menu.

Best souvenir: Headless Horseman logo items including T-shirts. Get them at the museum shops, or at Razzmatazz and Frank's Gifts on Route 9 off Main Street in Tarrytown.

Traffic alert: Although it's only 25 miles away, plan on at least 45 minutes negotiating traffic on a good day when coming from Manhattan.

Side Trip

Hudson River Museum

The Hudson River Museum (and planetarium) offers changing art, history, and science exhibits with a family focus.

Every Sunday at 1:30 p.m., make your own wind sock or participate in improvisational storytelling at the Family Workshop. And don't miss the museum's permanent collection. It includes Andy Warhol's Myth Series, featuring the likenesses of Santa Claus, Dracula, and the Wicked Witch of the West.

On the river at 511 Warburton Ave. in Yonkers, 20 minutes south of Tarrytown on Route 9 Phone: 914-963-4550

Reviewed April 2004.