Summary

• Lyndhurst After Dark: Experience the eerie beauty of the historic castle at night during Sleepy Hollow's annual Lyndhurst After Dark. Guided tours in candlelight reveal the property's paranormal activity. Perfect for all ages.
• Sleepy Hollow Cemetery Tours: Explore the spooky Sleepy Hollow Cemetery, a must-visit during Halloween. Day and night tours are available, with the nighttime lantern tour providing an extra touch of Halloween vibes (not recommended for kids).
• The Great Jack O'Lantern Blaze: Join one of the largest Halloween events in the area at The Great Jack O'Lantern Blaze. With over 7,000 hand-carved jack-o'-lanterns, atmospheric lighting, and sound effects, it's a family-friendly event not to be missed.

Along the eastern shore of the Hudson River and a mere 25 miles north of New York City lies the little village of Sleepy Hollow. This small community remains a modern-day household name because of Washington Irving's frightening classic "The Legend of Sleepy Hollow," which tells the story of Ichabod Crane and his unfortunate run-in with a headless horseman. This, of course, means that Sleepy Hollow, to this day, makes for a great place to celebrate Halloween in New York as the village inspired Irving for obvious reasons with its gloomy atmosphere and historic buildings like its Old Dutch Church. Here are some Halloween festivities one can only find in Sleepy Hollow.

UPDATE: 2023/09/29 17:33 EST BY NOAH STAATS

There Are More Fun Things To Experience In Sleepy Hollow This Fall!

This article has been refreshed with new things to do in Sleepy Hollow this fall and expanded information for each existing activity. This Upper New York town comes alive during Halloween, bringing spooks, scares, and plenty of memory-making opportunities to vacationers. Have fun!

11 Lyndhurst After Dark

• October 19th-22nd, 26th-29th, 2023
• Tickets: $20-$40 plus additional service fees

Something spooky to do this Halloween season in Sleepy Hollow is check out the city's annual '‎Lyndhurst After Dark' celebration, bringing the season to full fruition for residents and locals. This event is when people are allowed to tour the historic castle at night, with guided tours through the gorgeous complex draped in candlelight. This will be a bit eerie, as the property is known to have paranormal activity through the evenings. Luckily, there won't be people jumping out and scaring you, so this is okay for younger people and children. Lyndhurst Mansion is an iconic Upstate New York tourist destination, so why not see it in its glory at night?

This only happens during the Halloween season!

10 Sleepy Hollow Cemetery Tours

• Cemetery tours throughout Sleepy Hollow are in abundance during Halloween.

Exploring a spooky cemetery should be considered a staple in all Halloween celebrations, and Sleepy Hollow Cemetery provides a perfect place for this. A variety of both day and night tours are offered here, which vary in length and content. Those looking for full-on Halloween vibes should opt for the nighttime lantern tour, but be aware that it is not kid-friendly, and tour organizers request not to bring minors.

9 The Great Jack O'Lantern Blaze

• This celebration is family-friendly, boasting over 7,000 jack-o'lanterns.

A fantastic family-friendly option is one of the largest Halloween events in the area, the Great Jack O'Lantern Blaze. This event showcases over 7,000 hand-carved jack o'lanterns throughout its expansive grounds, which tie it all together with a scary soundtrack and atmospheric lighting and sound effects.

Related: Some Of The Best Places To See Grand Jack-'o-Lantern Displays Are Right In The US

8 Sleepy Hollow Street Fair

• This is a lively Halloween-themed market in town.

The Sleepy Hollow Tarrytown Chamber of Commerce hosts an annual Sleepy Hollow Street Fair, which turns Beekman Avenue into a lively Halloween-themed market (with a few things dedicated to the upcoming holidays thrown in). It takes place on the second week of October every year, and this year it will fall on Saturday, October 8th. This event helps transform the streets into Halloween as other festivities like parades, hayrides, and live music are in full force.

7 Tarrytown Halloween Parade

• This is a festival in the next-door town of Tarrytown, New York.

The vibrantly festive Tarrytown Halloween Parade, which has four times been named "Best of Westchester," typically begins at Patriot's Park and ends on Main Street. This parade which is a fabulous mixture of fun and macabre, makes its way across town until its finishing point, where festivities continue with a block party of food and live DJ sets.

6 Armour-Stiner Octagon House Myths And Mysteries Tour

• This is a guided tour and storytelling opportunity in town (focuses on the architecture and history of the area).

The domed landmark built in the 1860s, often referred to as the Octagon House, has been the subject of rumors of the supernatural throughout its entire history, including its residents' personal accounts of ghost encounters. Every October, the doors open for guests to take a tour to admire the architecture while hearing the unsettling details of the home's paranormal past.

5 Irving's Legend

• This is a story-telling attraction based on Washington Irving's "The Legend of Sleepy Hollow."

What would Halloween in Sleepy Hollow be without a recounting of Washington Irving's "The Legend of Sleepy Hollow"? Johnathan Kruk is hailed as a master storyteller who has been featured in The TODAY Show and Travel Channel, and here he provides hauntingly dramatic performances telling the story of the headless horseman among other local tales like The Wailing Woman in White and Mother Hulda, the Witch of the American Revolution.

4 Tarrytown Music Hall Ghost Tours

• This famed music hall is haunted, which becomes more apparent during the Halloween season.

This tour brings visitors through the Tarrytown Music Hall, built in 1885, in which some of history's most wealthy families, like the Rockefellers and Vanderbilts, would visit the venue for opulent balls, concerts, and other events. Famed storyteller Johnathan Kruk guides the way through this historical building that has endured depressions, wars, and sociopolitical events. It is part of the Haunted History Trail of New York and has been visited by the Gotham Paranormal Research Society.

3 Tour Washington Irving's Home

• Washington Irving's Home is a great fall activity for those interested in history.

Families with a deep interest in the story this town is famous for would love this daytime tour of Washington Irving's estate. Visitors can tour the home, learn about the origins of Washington Irving's classic story, and also see some artwork inspired by it. Additionally, guests have the opportunity to view never-before-seen treasures from the Historic Hudson Valley collection and participate in Headless Horseman arts and crafts.

Related: Studies Show This State Has The Biggest Halloween Vibe

2 Hulda's Night In Rockefeller State Park

• Hulda's Night brings guests through an eerie outdoor adventure in the Rockefeller State Park Preserve.

Hulda's Night takes visitors into an eerie outdoor setting at Rockefeller State Park Preserve, surrounded by the dark forest only with lanterns to light the way. This experience takes guests on a journey, including a lone storyteller recounting local legends around a fire, hearing the woes of a pastor of the Old Dutch Church in 1775 regarding witches and war in times past, and ends with a meeting with Hulda herself in the spot where her hut was rumored to be nearly 250 years ago.

1 Haunted Hayride

• Haunted Hayride in Sleepy Hollow is one of the top-rated Halloween events in town.

The Haunted Hayride is perhaps the best experience happening in Sleepy Hollow during this time of year for those looking to strike a little Halloween fear into their heart. The ride carries passengers through the gloom of Sleepy Hollow, over an old wooden bridge, and past the iconic Old Dutch Church as they can only wonder what awaits them out there in the dark. Hay rides will take place on October 21st and 22nd, with block parties at the starting point to entertain guests until it is time for departure. Tickets are on sale now and tend to sell out, so act quickly.