The Headless Horseman Rides Again! Halloween in the Hudson Valley

A bright blue sky, a chill in the air and a touch of gold on the leaves signals the onset of autumn in New York’s Hudson Valley and there is one Hudson River village that takes center stage at this time of year.  As the setting for Washington Irving’s famous Legend, Sleepy Hollow and its surrounding area has become one of the most iconic Halloween destinations in the country.  Just 20-miles north of New York City overlooking the majestic Hudson, Sleepy Hollow country plays host to myriad family activities throughout the season and visitors have plenty of haunted fun from which to choose.

The main player in the area’s Halloween offerings is Historic Hudson Valley (HHV), a not-for-profit organization whose mission it is to preserve and promote the Valley’s rich history.  A series of themed events, from the simply whimsical to the downright terrifying, are put forth by HHV beginning in October and continuing into November giving families lots of opportunities to celebrate the season of ghouls and goblins.

The Great Jack o’ Lantern Blaze – A Glowing Spectacle at Van Cortlandt Manor

Probably the favorite area event of the season, the Great Jack o’ Lantern Blaze, or just The Blaze as it has come to be known is celebrating its 10th anniversary this year.  For six weeks in October and November the Blaze treats over 100,000 visitors to the sight of more than 5,000 individually carved jack o’ lanterns.  Lead by Creative Director Michael Natiello, a small team of Historic Hudson Valley staff and local artists do the carving which results in a truly dazzling display.  In addition, more than 1,000 volunteers help scoop and light the pumpkins and Blaze artists will be carving pumpkins on site at HHV’s Van Cortlandt Manor during the event.

Our family has been to the Blaze several times and we look forward to new arrivals each year in addition to some of our favorites.  The kids choose a Halloween cookie and we all get some hot apple cider while waiting for our turn to enter.  When you purchase your tickets you can choose a time to arrive every 30-minutes between 6:30 and 9:00 pm.  The Blaze gets pretty crowded and the narrow pathway can be a little tricky to navigate with a stroller.  If your kids are younger, aim for a 6:30 pm slot.  The earlier slots often sell out first, with 7:00 and 7:30 being the most popular.

Horseman’s Hollow – A Frightful Evening at Philipsburg Manor

In a recent conversation with Rob Schweitzer, Director of Marketing and Public Relations for HHV, I joked that my 12-year old daughter still slept with her desk lamp on since attending the Horseman’s Hollow last season.  That said, she recently asked if she could go again this year.  The event takes place during 13 evenings at the historic Philipsburg Manor restoration, right in the heart of Sleepy Hollow.  Designed by haunted house professional Lance Hallowell, Horseman’s Hallow is a fully immersive, interactive, frightful experience geared toward older kids and adults.  Professional actors create a haunted village that is home to all variety of creepy inhabitants lead by the notoriously terrifying Headless Horseman.  This is not an event for the scaredy cats in the family and I wouldn’t recommend it for anyone under age 10.

The Legend Behind the Legend at Washington Irving’s Sunnyside

On the flip side, younger visitors will delight in an afternoon spent down the road in nearby Irvington at the historic property called Sunnyside, once the home of Washington Irving himself.  Tours of Irving’s riverside abode, shadow puppet tellings of the Legend of Sleepy Hollow, and woods walks with storytellers round out the activities.  Afterward, stroll through the village of Irvington or pack a picnic and enjoy the view of the sweeping Palisades from nearby Matthiessen Park.

Irving’s Legend – The Famous Tale Brought to Life

Those of us who live in the Hudson Valley area have most likely been treated, at one time or another, to the master storytelling of Jonathan Kruk, a valley local himself.  In his signature dramatic style, complete with different voices, costume and accompanying organ music, Kruk takes the stage again this year at the Old Dutch Church in Sleepy Hollow.  Kruk is a captivating storyteller and visitors of all ages will delight in his 45-minute retelling of the Legend of Sleepy Hollow.  Performances are Friday, Saturday and Sunday evenings beginning Saturday, October 4th and ending Saturday, November 1st with three times each evening from which to choose.

Historic Hudson Valley’s Halloween happenings are extremely popular and most sell-out fairly quickly. In fact, almost all of the Friday and Saturday night times for the Blaze are already completely booked.  However, I am thrilled to tell you that I have a family pack of 4-VIP tickets to this year’s Great Jack o’ Lantern Blaze to giveaway to one lucky reader.  These tickets entitle you to attend the Blaze any night this season even if it is already sold out.  These tickets also do not have a pre-determined time meaning that you may arrive whenever you wish.  Enter today!

Congratulations to Anja Steinmetz!  You’ve won this year’s Blaze tickets!

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