Best Sleepy Hollow Day Trip



If you have one day in Sleepy Hollow, NY, the most iconic Halloween town, we have crafted the perfect day trip for you. This itinerary is one that encompasses the very best of haunting history, chilling entertainment, and local culinary delights.



sleepy hollow cemetery toursSleepy Hollow Cemetery

First on our itinerary is a visit to the renowned Sleepy Hollow Cemetery. Known for its rich history and haunting atmosphere, this cemetery is the final resting place of many notable figures, such as Washington Irving himself, the author of The Legend of Sleepy Hollow. Others include Elizabeth Arden, Brooke Astor, Andrew Carnegie, Walter Chrysler, Samuel Gompers, and William Rockefeller.

Take a leisurely stroll through the cemetery grounds, surrounded by towering trees and crumbling tombstones, and feel the presence of the legends that inspired Irving’s iconic tale.

You can explore the cemetery on your own or join one of the guided tours that are offered periodically throughout the year. The tours range from one to two hours and cover different themes and areas of the cemetery.

You can learn about Washington Irving and his famous story, the titans of industry and philanthropy, the murder and mayhem that happened here, or the art and architecture of the monuments. Some tours are available at night by lantern light, adding to the eerie atmosphere. You can book your tickets online at:

You can also visit the adjacent Old Dutch Church, where the Headless Horseman supposedly chased Ichabod Crane in Irving’s story.

Sleepy Hollow Cemetery is a place where history, literature, and legend come together. It is a must-see for anyone who loves a good scare and a fascinating story.


sleepy hollow fall tours and events


The Legend Cirque

Next, watch Washington Irving’s tale come to life in the newest and most talked about addition to the Sleepy Hollow experience – by The Legend Cirque. Step into the magic of an intimate circus tent and witness gravity-defying story telling by aerialists and acrobats. In this totally immerse experience, The Legend Cirque takes you back to the 1800s. Watch Katrina Van Tassel (a witchy aerialist) at the center of the love triangle between Ichabod Crane (handbalancer) and Brom Bones (acrobat).

The performance features narration by Washington Irving himself, in hologram form. The Legend Cirque is a new and innovative way to experience the timeless tale of Sleepy Hollow.

The show is co-produced by Westchester Circus Arts and The Village of Sleepy Hollow. It runs from September 21 to October 29, 2023 at 60 Continental Street in Sleepy Hollow, NY. Tickets and information  can be found online at Don’t miss this opportunity to witness a spectacular and spooky cirque show that will leave you breathless.



After the show, it’s time to satisfy your hunger at Horsefeathers, a popular eatery since 1981 known for its delicious cuisine and cozy ambiance.

Horsefeathers is more than just a great place to eat. It’s also a place to relax, socialize, and appreciate the history and culture of Sleepy Hollow and Tarrytown. The walls are adorned with a mural featuring famous figures from literature, comedy, and music, as well as local landmarks and legends. You’ll feel like you’re part of the story as you dine in this historic setting.

The owner, a Sleepy Hollow enthusiast is also famous for the popular Instagram account that captures the essence of the town-

This Halloween, make the most of your day trip in Sleepy Hollow, NY. Immerse yourself in the chilling atmosphere of Sleepy Hollow Cemetery, witness the enchanting performance of The Legend Cirque, and treat yourself to a memorable meal at Horsefeathers. Don’t miss out on this extraordinary experience that combines history, entertainment, and culinary delights. Book your tickets early and embark on an haunting day you’ll never forget.


Pro tip: book all your tickets early.




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