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 2017.
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.
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.
2018 info: Horseman’s Hollow dates are October 5-7, 12-14, 19-21, 25-31. Online tickets are $20 ($25 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.
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.
Where: Sleepy Hollow Village Hall, 28 Beekman Avenue, Sleepy Hollow, NY 10591, 914-366-5100.
2018 dates: October 26 and 27, 7 pm until closing.
Tickets: go on sale late September.
The Old Dutch Church can be visited during the day for free, without the dramatic story-telling.
2018 info: Irving’s ‘Legend’ dates are Oct. 5-7, 12-14, 19-21, 25-31. Seating is very limited and there are three performances each weekday evening.
(Mon-Fri) 6:15pm, 7:30, 8:45
(Sat-Sun) 5pm, 6:30, 8
(Sat-Sun) 11:30am, 1:30pm, 3:30
Online tickets are $25 for adults, $20 for children under 18. Historic Hudson Valley members receive a $5 per ticket discount.
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.
2018 info: Sunnyside: Home of the ‘Legend’ dates are September 29-30, October 6-7, 13-14, 20-21, 27-28
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 for 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).
2018 Dates are October 5-7, 12-14, 19-21, 25-31 with 4 showings per night at 6:15pm, 7:15pm, 8:15pm, and 9:15pm.
Tickets are $18 each. There is a $5 discount per ticket for members.
Sleepy Hollow Cemetery
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.
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