Halloween Celebrations: The Villages of Sleepy Hollow & Tarrytown

The Hudson Valley is well known for weekend escapes to explore the villages packed with historic sites, recreational activities, award-winning restaurants, and lodging options that range from charming to over-the-top luxury. With the onset of autumn, a scenic drive along the Hudson River, taking the winding backroads, will surely get you in the mood for all things fall and the upcoming holidays. During the month of October, the must-stop destinations are the villages of Sleepy Hollow and Tarrytown, which, in combination, host some of the country’s best Halloween events and celebrations.

Things to Do

• Spend the evening with lantern in hand, wandering around Sleepy Hollow Cemetery, the final resting place of Washington Irving and other prominent local figures. The guided tours are exceptional and, for many, will be the highlight of the entire trip! The cemetery is open to the public, and maps highlighting the most popular sites are also available for a casual self-guided experience. Don’t forget to walk over to the Old Dutch Church, one of the locations mentioned in Irving’s spooky tale.
• Stroll through Historic Hudson Valley’s 2021 “Great Jack O’Lantern Blaze” at Van Cortland Manor, arguably the most popular Halloween event in the area. Gaze in awe at over 7,000 hand carved and illuminated pumpkins on a half-mile walk.
• Visit Washington Irving’s Sunnyside, the former home of the American author and creator of the Headless Horseman, Ichabod Crane, and Rip Van Winkle. Learn about the author and the nearby places that surely inspired his short stories.
• Listen to master storyteller Jonathan Kruk, as he delights audiences with Washington Irving’s short story “The Legend of Sleepy Hollow.” For 2021, the performance has been relocated to an outdoor venue at Washington Irving’s Sunnyside.
• Attend one of the special events or tours at Lyndhurst Mansion, including Spirited Mansion Weekend on October 29 – 31. The former home of railroad magnate Jay Gould is considered one of America’s finest examples of Gothic Architecture. Buy tickets for one of the seasonal tours, including the Fall Classic Mansion Tour, Backstairs Tour, and “Lyndhurst After Dark!”

Travel Tip: Obtaining tickets for each of the events can be challenging— dates on the weekends leading up to Halloween will sell out in hours. However, it is well worth the experience!! The best way to score tickets is to visit the Historic Hudson Valley website and signup for notifications about upcoming events and sale dates.

On a Return Trip

There are plenty of reasons to return to the villages of Sleepy Hollow and Tarrytown during the spring, summer, and autumn months. Keep an eye out of the 2022 opening dates for Kykuit, the Rockefeller Estate, Philipsburg Manor, and Van Cortlandt Manor. Spend a day at the Stone Barns Center for Food and Agriculture to participate in fun educational programs and learn about sustainable farming. The center is also home to the award-winning Blue Hill at Stone Barns, an unforgettable romantic culinary experience.

Featured Photo: Tom Nycz for Historic Hudson Valley