Sleepy Hollow at Halloween: Spooky Legends, Glowing Pumpkins & Ghostly Events | Day Trips from NYC

Описание: We visited Sleepy Hollow, New York right in the heart of Halloween season, and let’s just say it was everything we could ever hope for: full of lore, history, and a healthy dose of spine-tingling goosebumps.

We kicked things off at The Headless Horseman Files at Philipsburg Manor — an immersive theater mystery where we joined the ‘Who Dunnit?’ type of investigation — where we met some legendary characters (including Brom Bones himself!), and tried to uncover what really happened that fateful night of the iconic ride. From there, we wandered through Twilight Village, where a medley of live music, fire performers, and local vendors helped transform the scenic riverside into a Halloween festival. And of course, no Sleepy Hollow trip during spooky season is complete without dropping by The Great Jack O’Lantern Blaze, where thousands of glowing pumpkins lit up the night in the most magical, eerie way imaginable.

Midday caffeine was a must, so we hit up Sleepy Coffee Too, for a treat and the vibe was as cozy as the name suggests. As for lunch? Brom Bones (the actor, staying perfectly in character) tipped us off to Goosefeather — which was upscale, delicious, and turned out to be a fantastic call.

Overall, a fun time was had! What struck us most about this upstate New York destination was how deeply The Legend of Sleepy Hollow by Washington Irving is woven into the fabric of everyday life here. From themed store decor to local street signs to police cars, the horseman logo is pretty much ubiquitous and a vital part of the town’s identity. If you love fall, folklore, and a bit of theatrical flair, Sleepy Hollow is pure Halloween perfection. 🕯️🍂💀🎃

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