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When autumn arrives and the leaves turn bright colors in the Hudson Valley, Sleepy Hollow and Tarrytown become a Halloween wonderland full of stories and spooky charm. No matter if you love a good scare, enjoy history, or just want some fall fun, this part of New York has something memorable for everyone.

This year, I decided to visit Sleepy Hollow in late September to avoid the Halloween crowds. Even then, decorations were already up on houses, shops, schools, and even one of the local funeral homes.

The day was warm and humid, but the cloudy sky set the perfect mood for an early Halloween tour.

🪦 Sleepy Hollow Cemetery Tours

Sleepy Hollow Cemetery is the resting place of Washington Irving, author of The Legend of Sleepy Hollow, and a centerpiece of the region’s Halloween festivities. Throughout October, the cemetery hosts a variety of events:

• Take a daytime guided walking tour to explore the 90-acre grounds and discover the stories of notable people buried here, such as Irving, Carnegie, and Helmsley. Take the Original Knickerbocker Tour to learn about Irving’s life and legacy on a guided walk that brings together literature and local history.
• Join an evening lantern tour and walk through the cemetery by lantern light while guides share chilling stories about local legends and ghostly happenings.
• Experience special performances with dramatic readings of stories like The Strange Case of Dr. Jekyll and Mr. Hyde: The classic Gothic tale of good versus evil will be performed on Saturday, October 11, 2025, at 6:30 p.m. and 8:30 p.m. by master storyteller David Neilsen.
• Bram Stoker’s Dracula: A dramatic reading of the vampiric masterpiece will take place on Sunday, October 12, 2025, at 6:30 p.m. and 8:30 p.m

Tarrytown Halloween Highlights

Right next door, Tarrytown has a great mix of family fun and just the right amount of spooky excitement.

• Tarrytown Halloween Parade: A lively procession of costumes, floats, and music followed by a community block party.
• Spooky (But Not Too) Scary Stories: Legendary storyteller Jonathan Kruk enchants audiences at the Tarrytown Music Hall with tales like The Haunted Hand and The Witch’s Surprise.
• Window Painting & Scarecrow Making: Local kids and artists decorate the town with Halloween-themed art.
• Historic Tours: Learn about Tarrytown’s rich past through guided walks and museum visits.

🍂 HorseFeathers

After a fun day of touring the rounds in town, we capped it off with dinner at Horsefeathers (always enjoyable), which will soon be nearly impossible to get into. If you’re in Sleepy Hollow Country for Halloween, be sure to visit Horsefeathers (but go early). This welcoming spot features:

• Seasonal Cocktails & Mocktails: Sip themed drinks like the Pumpkin Espresso Martini, Apple Sangria, Fallen Apple, and Apple Cider Whiskey Smash. Or enjoy a non-alcoholic hot cider.
• Hearty Fare: Enjoy tavern comfort classics like the Roast Turkey Dinner (which I ordered), the Shepherd’s Pie (a vegetarian version is available), or the playfully named Ichabod Cod. And try the Bailey’s Bread Pudding for dessert.
• Atmospheric Decor: Flickering lanterns, vintage portraits, and touches inspired by the Headless Horseman create a true Halloween vibe.
• Live Entertainment: Catch local bands and storytellers performing throughout October.

🗺️ Plan Your Visit

Events fill up fast, so it’s a good idea to reserve your cemetery tours and tavern spots early. Whether you’re hunting for ghosts, carving pumpkins, or just enjoying some cider, Halloween in Sleepy Hollow and Tarrytown is full of fun and surprises.

Don’t lose your head. Join the celebration!