Beyond City Limits / Halloween / Travel

A Sleepy Halloween – Exploring Sleepy Hollow


There’s no better way to celebrate the spooky season than by experiencing Historic Hudson Valley’s Halloween events in Sleepy Hollow Country.  With events such as the incredible Great Jack O’Lantern Blaze, the frightening Horseman’s Hollow, telling of Washington Irving’s famous story, and a tour of one of the worlds spookiest cemeteries – there is no better place to take in Halloween! We love Sleepy Hollow, and our family has traveled there annually to kick off the ghostly season. Read on to learn more about our favorites, and the must see attractions in Sleepy Hollow.

A Sleepy Halloween – Exploring Sleepy Hollow

Legend Behind the Legend Sleepy Hollow

Legend Behind the Legend
Start your day in Sleepy Hollow where the story began with a tour of Washington Irving’s home. On this tour you are able to access both floors of his house, hear stories about what inspired Irving to write his famous short story and also see works of art inspired by The Legend of Sleepy Hollow. The tour features a display of special edition books to pop culture artifacts as well. After, play historic games and Headless Horseman art activities, all of which are great for families.  This daytime event is the perfect for history buffs, little kids who would not enjoy the spooky nighttime activities, and is a great prelude to an evening at Blaze, Horseman’s Hollow. Be sure to walk the grounds to enjoy the fun photo opps.
Legend Behind the Legend. Located at Washington Irving’s Sunnyside. 3 W Sunnyside Lane, Irvington, NY 10533. More information HERE.

The Headless Horseman at the Old Dutch Church of Sleepy Hollow

Headless Encounter

The Headless Horseman rides again every weekend in Sleepy Hollow! The Old Dutch Church of Sleepy Hollow (technically known as the Reformed Church of the Tarrytowns) will host the annual Old Dutch Church Fest every weekend in October, from noon to 4 p.m. Famed storyteller Jonathan Kruk will perform readings of The Legend of Sleepy Hollow in the old church. An “Oktoberfest” style refreshment tent right on the burial grounds offers hotdogs, bratwursts, and apple cider for kids, and even pumpkin ale for moms and dads. Children will enjoy the free scavenger hunt through the cemetery – which if you complete there is a small prize. Don’t forget to have their picture taken with the Headless Horseman who YES actually rides through the graveyard… a sight that must be seen to be believed.
Old Dutch Church Fest. Old Dutch Church of Sleepy Hollow. .Entry, talks and tours are free; tickets to the “Legend” performance are sold HERE. Proceeds from this year’s Fest will go toward the restoration of two dozen historic stones and monuments in the Burying Ground. Read more about the church HERE.

Walking through the graveyard of Sleepy Hollow


Cemetery of Sleepy Hollow
A trip to Sleepy Hollow isn’t complete without a visit to Sleepy Hollow Cemetery and its famous residents. Elizabeth Arden, Brooke Astor, Walter Chrysler, Washington Irving, and William Rockefeller, among thousands of others, are buried here in these grounds adjacent to the Old Dutch Church. Even more famous then these residents is how the cemetery is forever linked to one of the best known Halloween tales, The Legend of Sleepy Hollow. In the story written by Washington Irving, Ichabod Crane is chased towards the Old Dutch Burying Grounds by a Headless Horseman. The cemetery’s connection to the story doesn’t stop there; Irving, himself, is buried here. Grab a free map to locate Irving’s final resting place and explore all 90 acres of one of the most scenic and famous cemeteries in the world. This cemetery has it all – decaying 18th century headstones, twisting narrow paths, and eerie metal gates, all makes for a straight-out-of-a-movie Halloween scene that simply cannot be replicated anywhere else. A must see.
Sleepy Hollow Cemetery. 540 North Broadway, Sleepy Hollow, NY. More information on the cemetery HERE. In October, the cemetery hosts ghost stories by Washington Irving. For younger children there is shadow puppetry, for older children Spooky Stories! Check links for dates/times.


Horsemans Hollow Haunted AttractionImage courtesy of Horseman’s Hollow

Horseman’s Hollow
Of course there is a Haunted attraction featuring the tale of The Legend of Sleepy Hollow and the Headless Horseman! Philipsburg Manor transforms into a landscape of terror ruled by the evil, the undead, and the insane during the month of Halloween. Visitors start the experience by walking a haunted trail, stumbling upon scary scenes of a town driven mad by the Headless Horseman. Creatures lurk in the shadows throughout the attraction, ready to terrify the unsuspecting visitors while incredible special effects, elaborate costumes and the work of award-wining feature-film makeup artists make it all very real. Heads will definitely roll…maybe even your own! This is Sleepy Hollow’s premier haunted attraction, right in the heart of the village. Most nights SELL OUT IN ADVANCE. I’ve personally seen this show, and it is SCARY… and definitely not for young kids. Recommended for ages 10+.
Horseman’s Hollow. Philipsburg Manor. 100 Continental St., Sleepy Hollow, NY. More information and tickets HERE.


The Blaze Pumpkin Scene

A Blaze-ing Pumpkin Scene
No need to wait for the Great Pumpkin to appear to see a Halloween display, head to the famous Great Jack O’Lantern Blaze!  The Blaze is an annual Halloween extravaganza in the Hudson Valley with over 7,000 carved jack o’ lanterns and pumpkin sculptures that brings in over 175,000 visitors each year! A great day trip for fans of Halloween, art or pumpkin carvings! Interested in tickets? Act quick! Days and times sell out in a blink.  We love this event, and have attended many times over the years. Read our full review HERE.  
The Great Jack O’Lantern Blaze. Runs through October/early November. Van Cortlandt Manor. 525 S Riverside, Croton-on-Hudson, NY 10520. More information HERE.


Horsefeathers in Tarrytown

Scare up an appetite? We love grabbing a bite at the charming Horsefeathers in Tarrytown, which is just a short drive from the cemetery. Serving up to 100 different menu items daily, there is something here for everyone in the family, no matter how picky they are! There is a sidewalk patio if the weather is warm, or dine inside in a welcoming dining room surrounded by amazing murals and Halloween decor.  After – take a short walk to the charming main street in Tarrytown where there is a toy store, additional restaurants, and local stores. Horsefeathers is a great Halloween-themed family food stop while hopping around the town’s festivities.
Horsefeathers. 94 North Broadway, Tarrytown, NY. Website and menu  and children’s menu HERE.



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