Apple orchards, corn mazes, and pumpkin patches are traditional autumn activities. But tradition isn’t always good. In this case, it leads to the expected flood of carbon copy pictures.
Your goal might be to create a better Instagram post or simply experience something new, either way, Sleepy Hollow is exactly what you never knew you needed. About an hour away from Sayreville, Sleepy Hollow lies tucked away in the Hudson Valley.
The village was established in the early 1600s, originally known as “Slapershaven,” which is Dutch for “sleepers haven”. Later, during the 1800s, it was named “North Tarrytown.” It received its current, official name, “Sleepy Hollow” in 1996.
The abundant amount of headless men on horse decorations might throw you off during your visit, but fear not, this is the famous headless horseman myth: The story, The Legend of Sleepy Hollow, written by Washington Irving, heavily impacts the village. Ichabod Crane, a teacher, attends the party of a wealthy farmer, Baltus Van Tassel. During this party, ghost stories are told, particularly about the headless horseman. When the party ends, Ichabod is upset due to being rejected by Baltus’ daughter, Katrina. Along with the humiliation swirling in his mind, the ghost stories creep their way in as well. He comes across the headless horseman, who then begins to chase him. The man throws his head at Ichabod, knocking him out. The next morning, Ichabod’s hat and a smashed pumpkin are all that’s left.
There are many adaptations of this story. The Headless Horseman, a 1922 silent film, is closest to the original, with the exception of Ichabod’s headless horseman encounter. Though the Disney princesses might have been your childhood cartoons of choice, for some, it was The Adventures of Ichabod and Mr. Toad, a 1949 Disney animated film based on the Sleepy Hollow story, but with a family-friendly and light-hearted tone.
On the opposite end, Tim Burton’s 1999 Sleepy Hollow film leans toward the murder mystery genre. Its small difference is that Ichabod is a constable sent to investigate the series of murders in Sleepy Hollow, which ultimately leads to the headless horseman.
The farthest from Irving’s story, Fox’s 2013 TV series, Sleepy Hollow, explores a modern supernatural interpretation. A resurrected Ichabod Crane and police lieutenant Abbie Mills join together to fight against supernatural threats linked to the apocalypse, the headless horseman being one of them. Although these films and series differ, they are all inspired by Irving’s story, showcasing what a classic The Legend of Sleepy Hollow is.
From books to film, Sleepy Hollow, New York, has grabbed the attention of many. Prepare to immerse yourself in that very same transformative atmosphere with this itinerary.
Horsefeathers, a restaurant with a hip reputation, sets the mood with their 2000s playlist, warm candlelit atmosphere, and fall decorations. The environment is enjoyable, but the food is the cherry on top. The menu features seafood, pastas, burgers, sandwiches, meats, and to satisfy your sweet tooth, there are options from strawberry shortcake to a vanilla ice cream sundae with a brownie center, topped with chocolate syrup and whipped cream. (Your salivary glands must’ve been activated just now.)
Now that you have the restaurant portion of your agenda complete, let’s go over the must-see events. The Craft and Street Fair downtown is full of vendors selling handmade crafts, thrifted clothes, rare collections, jewelry, and much more. If you want to separate from your pestering younger sibling then drop them off at the bouncy house. On your way to the bouncy house, your nose will pique with curiosity because of the smell of the various food trucks. For everyone’s taste buds, there’s traditional Greek food, lobster, pizza, or the classic American hot dog. You’ll feel as if you’re in a casino with the way you spend the day here without noticing the passing time.
“You don’t have to be from Tarrytown to know that Halloween here is a big deal,” Andrew Ramos, a CBS New York reporter, said in reference to Sleepy Hollow’s Halloween parade. Upon arrival, you’ll experience unique parade floats, street dance performances, families dressed up head to toe, free candy, talented marching bands, large groups of roller skaters, and the man of the hour: the headless horseman himself . Before your adrenaline runs out, head over to the mini concert and sing along with the band. What better way to bring the community together than wearing a mask and dancing with strangers?
Keep in mind, the Craft and Street Fair and the Halloween Parade have already taken place this year, but you can always go next year. If you are still looking to fill up your weekend plans for the remainder of autumn, there are some upcoming events.
If you’d like something earlier in the morning, then, from 9 am – 1:30 pm, on November 16, there is the Irvington Farmers Market, free to attend. You can “Enjoy live music, river views and a laid-back setting…[with] fresh local produce, seafood and meats, cheese, pickles, prepared foods and baked goods,” according to the Sleepy Hollow website.
Bring out your fancy suits and dresses for the Taconic Opera presenting Turandot. It will be held in the Tarrytown Music Hall on November 16 from 1:00 pm to 2:30 pm, and the cost is $20 – $81 to attend.
The Sleepy Hollow Cemetery Lantern Tour is a trip back in time, allowing visitors to see the resting places of historical figures such as Andrew Carnegie, William Rockefeller, Washington Irving, and Walter Gurnee. Unique from typical cemeteries, this one has beautiful architecture, scenic landscape, and detailed tombstones. It will be held on November 22 from 7 pm – 9 pm, and the cost is $50 to attend.
Or you could ignore everything listed and just go downtown! You’ll be lavished with numerous local businesses like boutiques, book shops, cafes, florists, art, and…I don’t want to spoil anymore, go see it for yourself!
Who knew your perfect Autumn visit awaited in a quaint village?
For further events and information check out https://visitsleepyhollow.com/

















