Plan a spooky family outing to the home of the Headless Horseman this Halloween season.

Historic Sleepy Hollow country in Hudson Valley, New York offers a range of activities celebrating Washington Irving’s classic haunted tale. That makes it perfect for a day trip or a weekend getaway! Here is a rundown on the events you can enjoy in Sleepy Hollow Country this Halloween season.

Sleepy Hollow Country

“In the bosom of one of those spacious coves that indent the eastern shore of the Hudson… there lies a small market-town… known by the name of Tarry Town… Not far from this village, perhaps about two miles, there is a little valley… This sequestered glen has long been known by the name of SLEEPY HOLLOW.”

Follow the Hudson River north from New York City for about 25 miles and you’ll come to the home of Washington Irving, famous for being one of the first American authors.  Views of the forest-lined river make this area quite beautiful, especially in the fall.

Irving described this region, writing: “A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.” It’s a great area to visit, especially around Halloween, since the “the whole neighborhood abounds with local tales, haunted spots, and twighlight superstitions.”

In my opinion, it’s the perfect place to enjoy a warm apple-cinnamon donut and a hot apple cider while listening to a spooky tale on a crisp, October evening.

The Legend of Sleepy Hollow

I love ghost stories.  To me, the “Headless Horseman” is the most iconic of all ghosts when it comes to Halloween. The guy carries a Jack-o-lantern in place of his missing head! He’s the coolest ghost ever!

I think I was about 10 or 11 years old when I first heard the story of Ichabod Crane and the Headless Horseman.  I think it’s a great tale to share with the kids! Disney’s classic animated version (narrated by none other than Bing Crosby) can be found online. You can also also purchase a young reader’s version of The Legend of Sleepy Hollow from Amazon.

Halloween in Hudson Valley

“Sleepy Hollow Country” embraces its history each Halloween with events that celebrate Irving’s classic tale.  Some of the events may not be suitable for younger children, but there’s still plenty of reasons to consider making a family day trip or weekend visit.

The Great Jack O’Lantern Blaze

The Great Jack O’Lantern Blaze has become our family’s favorite Halloween tradition.  We’ve seen some other Jack O’Lantern displays over the years, but this is the best.  In my opinion, THIS is the event you want to plan your visit to Sleepy Hollow around.  It’s perfect for the whole family.  Want to know more? Here are 5 reasons you should experience the Blaze!

Each year, over 7,000 pumpkins are hand carved and then arranged to create an experience like no other.  Alien landscapes, giant snakes, spider webs, dinosaurs, sea serpents, skeletons… and of course, the Headless Horseman and famous Sleepy Hollow Bridge.  Here is our video of the Great Jack O’Lantern Blaze from 2018.

2019 Info:

Where: Van Cortlandt Manor, Croton-on-Hudson, NY
When: Sept. 20-22; 26-29, Oct. 3-31, Nov. 1-3, 8-10, 15-17, 22-23, and 29-30.
Price: Online tickets are $23 for adults ($29 on Fridays and Saturdays), $17 for children 3-17 ($22 on Fridays and Saturdays), and free for children under 3 and Historic Hudson Valley members.

I strongly suggest purchasing tickets in advance.

The Great Jack O’Lantern Blaze has been the sole reason for our annual Halloween visit to Sleepy Hollow Country so far, but you can explore more of the story with these other experiences.

Horseman’s Hollow

Billed as an “outdoor/indoor ‘period-correct’ haunt”, Horseman’s Hollow is a ticketed event that takes you into the world of a village taken over by the Headless Horseman himself.  If you’re looking to be scared, this sounds like it’s for you.

It’s not suitable for young children or for adults who are claustrophobic, or have heart or other health conditions.  This is something I would like to experience, but I know that Lisa and the kids would not enjoy it.

2019 info: 

Where: Philipsburg Manor, Sleepy Hollow, NY
When: October 4-6; 11-13; 18-20; 25-27; 31; November 1- 3.
Price: Online tickets are $20 ($28 on Saturdays). Fast Track, a $15 per ticket upgrade, lets visitors skip the line in their time slot. Historic Hudson Valley members receive a $5 per ticket discount.

Sleepy Hollow Experience

Imagine being a part of the story of Ichabod Crane and the Headless Horseman. The Sleepy Hollow Experience is an immersive theater experience that does exactly that. There are no chairs. You literally follow the actors from scene to scene and are part of the story.

After being performed around the country over the past few years, the Sleepy Hollow Experience will be held at the very home of the story’s creator.

2019 Info:

Where: Washington Irving’s Sunnyside, Tarrytown, NY
When: October 4-6, 10-13, 17-20, 24-27, 31; Nov 1-3. Performances at 6:30pm and 8:30pm
Price: Adults: Starting at $45; Children 3-17: Starting at $25; Members: 10% discount/ticket; Children under 3: FREE, no ticket required.

Haunted Hay Ride

For one weekend each Halloween, the town of Sleepy Hollow hosts a Haunted Hayride that follows the same path Ichabod Crane is said to have taken the night he was chased by the Headless Horseman.  (Irving made up the story, but used real landmarks in his descriptions).

In addition to the hayride, there is a free block party with activities for the whole family.  This year, the event is taking place the weekend before Halloween.

2019 info:

Where: Sleepy Hollow Village Hall, 28 Beekman Avenue, Sleepy Hollow, NY 10591, 914-366-5100.
When: 2019 dates: October 25 and 26, 7 pm to 11pm.
Tickets go on sale late September.

Irving’s ‘Legend’

Irving’s ‘Legend’ is a faithful retelling of Irving’s classic, The Legend of Sleepy Hollow.  The story is told by a live actor in the Old Dutch Church in Sleepy Hollow.  The website does not recommend this experience for younger children.  I think Lisa and Bella could handle this.  It may be a few years before the whole family gives this a try, though.

The Old Dutch Church can be visited during the day for free, without the dramatic story-telling.

2019 info: 

Where: Old Dutch Church, Sleepy Hollow, NY
When: October 4-6; 11-14; 18-20; 25-27; 31; November 1-3. Seating is very limited and there are three performances each weekday evening.
Price: Online tickets are $28 for adults, $22 for children under 18. Historic Hudson Valley members receive a $5 per ticket discount

Performances starring Jonathan Kruk:
(Thu-Fri) 6:15pm, 7:30, 8:45; (Sat-Sun) 5pm, 6:30, 8

Performances starring Jim Keyes:
(Sat-Sun) 11:30am, 1:30pm, 3:30.

Sunnyside, Home of the ‘Legend’

Visit and explore ‘Sunnyside’, the home of Washington Irving.  Sunnyside, Home of the ‘Legend’ includes a tour and family-friendly activities such as Halloween-themed art activities, a literature-themed scavenger hunt, historic games, a spooky photo op, and a shadow puppet performance.

Pairing “Sunnyside, Home of the ‘Legend'” with the Great Jack O’Lantern Blaze is the best option for families with younger children.  Leave yourself time in between to get something to eat, but leave room for snacks at the Blaze.

2019 info: 

Where: Washington Irving’s Sunnyside, Tarrytown, NY
When: September 28-29; October 5-6; 12-14; 19-20; 26-27; November 2- 3. Price: Online tickets are $16 for adults, $12 for seniors/students, $8 for children 3-17, and free for those under 3 and Historic Hudson Valley members.

The Unsilent Picture

New in 2018, this original film was shot in Sleepy Hollow Country. It’s based on a spooky tale by Washington Irving and each viewing has live musicians providing the soundtrack and live sound effects being provided by a Foley artist. (That’s the way sound was provided for films way back in the day).

2019 Info:

Where: Philipsburg Manor, Sleepy Hollow, NY
When: October 4-6; 11-14; 18-20; 25-27; 31; November 1- 3
Sat-Sun: 12:45pm; 2:45; 4:45, 6, 7, 8, 9*
Friday + Oct 31: 6pm, 7, 8, 9 Columbus Day: 12:45pm; 2:45; 4:45 *No 9pm performance on November 3
Price: Tickets are $15 for adults, $10 for children. There is a $5 discount per ticket for members.

Sleepy Hollow Cemetery

The final resting place of Washington Irving offers Halloween events and guided tours both during the day and lantern tours in the evening.  While not “scary”, this is not something I would take the kids to right now.  Maybe when they are older.

Places to Stay

There are several hotels, inns, and bed & breakfasts in the area.  Some of the area hotels run specials for the Halloween events.

Being just 25 miles from New York City, you could also plan your stay around a visit to the Big Apple.

For more info on Sleepy Hollow area options, check out the Visit Sleepy Hollow site.

Planning your Visit

We’re fortunate to live close enough to visit each year.  We’ve yet to make a full day experience of it yet.  Typically, we buy our tickets for the Great Jack O’Lantern Blaze and work out if we’ll have dinner beforehand or afterwards.  Perhaps this year we will make more of a day of it, checking out the town of Sleepy Hollow and perhaps stopping by Sunnyside.

We could also work in other fall favorites, like apple or pumpkin picking during the day before seeing the Great Jack O’Lantern Blaze in the evening.

If this sounds like something you’d like to do with your family or friends, check out Historic Hudson Valley’s planning guide. It has some great tips on how much time you’ll need to allow for doing multiple ticketed events on the same day.

Which of these Sleepy Hollow treats most appeals to you and your family?  Let us know in the comments below.

For more Fall fun, check out the other great posts from our friends!

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