Halloween in Sleepy Hollow

Hi Readers! The spookiest month has finally arrived, so this week we’ll be diving in for the best places to visit to celebrate Halloween. One of these locations is Sleepy Hollow, New York, where Washington Irving’s famous tale “The Legend of Sleepy Hollow” took place. This is the story that involves the notorious headless horseman, thus many activities that take place are themed around this character. There are plenty of events for the whole family to enjoy, but the truly unique ones to this town are some of the spookiest Halloween festivities that you can partake in. Keep reading for a haunted itinerary!

Transportation

A visit to Sleepy Hollow would make the perfect long weekend adventure, so if you live close enough to New York I’d recommend driving. If not, the closest airport is the Westchester County Airport or LaGuardia Airport. Once you arrive, rent a car and head over to Sleepy Hollow, a half hour or hour’s drive respectively.

Lodging

             Because Sleepy Hollow is such a quaint place, there are actually no hotels in the town itself. However, close neighbor Tarrytown is a five-minute drive away and offers a really unique, beautiful hotel called the Castle Hotel and Spa. It is a historic castle property built in 1897 that offers plenty of amenities such as a restaurant, outdoor pool, walking trails, picturesque rooms, and much more.

Food

 Breakfast

Start your day with breakfast in Tarrytown, then head on over to Sleepy Hollow for all the Halloween activities. Best places to enjoy some morning grub include:

• Bagel Emporium
• Bellas Restaurant
• Landmark Diner

Lunch and Dinner

•  Hudson Anchor Seafood & Grill – offers dishes from both the land and sea, with a rooftop deck overlooking the Sleepy Hollow Lighthouse. Brunch is also served here on the weekends
• Hudson Farmer & the Fish – great views of the Hudson River with a full raw bar, seafood, and pizza
• P. Doyle’s Restaurant & Public House – Irish pub with outdoor beer garden
• Red Zebra – modern Italian cuisine
• Blue Hill at Stone Barns – upscale restaurant opened by famous Manhattan chef Dan Barber
• Equus – high class restaurant located in your hotel

Dessert

• Los Andes Bakery – traditional Chilean pastries located right in Sleepy Hollow
• Main Street Sweets – located in Tarrytown, so you can load up on some homemade ice cream, pies, and cookies on your way back to the hotel

Activities

• The Great Jack O’Lantern Blaze – This is one of the largest Halloween events across the nation, and is truly an unmissable experience for your Hallo-weekend adventure. It takes place in the neighboring town of Croton-on-Hudson, and features over 7,000 hand carved Jack O’Lanterns.
• Horseman’s Hollow – This is the scariest, more haunted attraction that brings Irving’s tale to life. The town turns the 400-year-old Philipsburg Manor into a dark, evil village ruled by the Headless Horseman that is guaranteed to give you the scare of your life. Don’t bring the kids to this one!
• Irving’s Legend – Enjoy a spooky performance of “The Legend of Sleepy Hollow” in the candlelit Old Dutch Church filled with live organ music and dramatic storytelling.
• Sleepy Hollow Cemetery Guided Tours – Not only is Washington Irving buried here, but many other infamous people such as Andrew Carnegie and William Rockefeller. Both daytime and lantern-lit tours are offered in this 85-acre cemetery, and are guaranteed to be both spooky and informative. There’s even an option for a tour called “Murder & Mayhem” which highlights some of the darker aspects of the cemetery, sure to give visitors a scare and a thrill.