REVIEW Sleepy Hollow Halloween: Great Jack O Lantern Blaze and Legend Behind the Legend

As soon as I saw images of life-sized dinosaurs built from carved pumpkins, I knew our family had to go to the Great Jack O Lantern Blaze in Sleepy Hollow, NY.  After years of trying, we finally took the spectacularly scenic fall drive from Rochester to Tarrytown, New York (home of Sleepy Hollow) over Columbus Day weekend.  From early October to mid November, New York’s Historic Hudson Valley embraces its most famous tale with the Great Jack O Lantern Blaze – imagine the biggest, brightest, most over-the-top holiday light display, switch out Christmas lights for pumpkins, and you start to get a sense of Blaze.  However, Blaze isn’t the only thing haunting Sleepy Hollow over Halloween.  There are even more spooky events, and I swear there’s a ghost hanging over the land.  Continue reading for more photos and impressions of Halloween in Sleepy Hollow, NY.

Great Jack O’ Lantern Blaze

Thousands of visitors flock to Sleepy Hollow to see The Great Jack O Lantern Blaze each year.  The event often sells out, so be sure to buy your tickets ahead of time through the Historic Hudson Valley website.  Also, as you get close to the historic Van Cortlandt Manor, home of the event, you’re traveling roads not made for thousands of cars, so give yourself plenty of time to park and get to the event.  But once you arrive, oh, what a sight!  Fields upon fields of lit, carved pumpkins, animated displays, and changing lights.

Great Jack O’ Lantern BlazeGreat Jack O’ Lantern Blaze

In addition to the aforementioned pumpkin dinos, you’ll find an undersea pumpkin aquarium, sea serpents, spider webs, monsters, witches, and more.  I’m not just talking about individual carved Jack O’Lanterns either (though there are certainly plenty of those).  No, I’m referring to gargantuan squash displays – like a 50-foot tall spider web constructed from hundreds of gourds.

Great Jack O’ Lantern BlazeGreat Jack O’ Lantern Blaze

Of course, it wouldn’t be Sleepy Hollow if there wasn’t a reference to the Headless Horseman, and multiple scenes from The Legend of Sleepy Hollow story are re-created in pumpkin form, including: Van Tassel’s farm house, an ominous Grandfather clock striking twelve, the covered bridge, and the infamous Hessian rider tossing its flaming pumpkin-head.

Great Jack O’ Lantern BlazeGreat Jack O’ Lantern BlazeGreat Jack O’ Lantern BlazeGreat Jack O’ Lantern Blaze

Pumpkin carving for Blaze begins in June, and nearly 10,000 are chiseled throughout the Great Jack O Lantern Blaze’s run.  Artisans work continuously to replace the rotten and collapsing fruit.  This year, The Great Jack O Lantern Blaze celebrates its 10th anniversary, and continues to bring in more and more visitors to the area.  In 2013, over 100,000 people flocked to the site to witness the display.  So pack your patience, prepare for some walking and waiting, and get ready to be amazed.  But what about that ghost I mentioned?

Great Jack O’ Lantern Blaze

Following our long drive and evening at Blaze, we looked for a less intense activity to spend Sunday afternoon in Sleepy Hollow.  The Legend Behind the “Legend” was just our speed.  On the grounds of Washington Irving’s Sunnyside homestead, along the Hudson River, was a daytime celebration of the author and his most famous tale.

Washington Irving's Sunnyside

We lucked out with a spectacular Autumn day, and enjoyed the sunshine while listening to storytellers.  We played 19th century games (hoops and graces) outdoors, and viewed objects related to and inspired by The Legend of Sleepy Hollow on display inside Irving’s house.  Our favorite activity was the shadow-puppet re-telling of The Legend of Sleepy Hollow; we were so impressed with the period performance.

Legend Behind the Legend at Washington Irving's Sunnyside

Photo by Tom Nycz, courtesy Historic Hudson Valley


There were also guided “spooky” walks through the surrounding woodland paths where a docent recounted Washington Irving’s Devil and Tom Walker.

Legend Behind the Legend at Washington Irving's Sunnyside

We took advantage of the unseasonably warm October day to be silly, play games, and pose for photos in the cut-outs.  Behold, Evie-bod Crane flees the Evie-less Horseman!

Legend Behind the Legend at Washington Irving's Sunnyside

However, we sensed a presence… strange things occurred throughout the day, a purse left behind, a walking stick gone, a camera disappeared, and we figured out – that Horseman’s a trickster!  The Hessian rider must still be haunting the grounds stirring up mischief with the visitors.  Seriously, Sleepy Hollow bursts with activity during the Halloween season, and everywhere you look one can find references to the Headless Horseman.

Sleepy Hollow, NYSleepy Hollow, NYSleepy Hollow, NY

The historic village is a great place for families to visit.  It’s close enough to New York City for an easy day trip on the train, and not that far for a weekend getaway road trip from Western New York.  There are plenty of activities to entertain, and our family didn’t even get to the other signature events in the Valley: Horseman’s Hollow and Irving’s Legend.  We’ll just have to come back next year for those.

Sleepy Hollow, NY

Tappan Zee Bridge, 1883 Sleepy Hollow Lighthouse, and Manhattan in the distance

Bridge View Tavern, Sleepy Hollow, NY

Sleepy Hollow has plenty of eateries lining its main drag, and we thoroughly recommend dinner at the Bridge View Tavern, a hip pub with tons of craft beer.  Of course I had to get a pint of the Ichabod Pumpkin Ale.  When the bartender asked, “do you want sugar on the glass?”  I said, “why not?”  And he served it with a rich head and a glass rimmed with sugar crystals, nutmeg, and pumpkin spices.  Oh, and the burgers, BBQ, and steaks delectable good too!

We loved our weekend in Headless Horseman country, but just beware of the Hessian during your visit.  Don’t believe me?  Well, the Trickster even followed us home with a final joke that caused our daughters to miss school with a tummy-ache.

DISCLOSURE: The Historic Hudson Valley provided complimentary tickets to The Great Jack O Lantern Blaze and Legend Behind the “Legend” for the purposes of this review.  However, all opinions are those of the author.  For more family travel news, reviews, and trip reports, be sure to follow Adventures by Daddy on twitter and “like” our facebook page too.

About Dave Parfitt

Married, father of two girls, and living in the heart of the Finger Lakes. I'm a runner with a PhD in neuroscience and a passion for travel.