Sleepy Hollow, NY is the perfect place to visit for a Halloween season getaway! The village is somewhat small so a weekend is the perfect amount of time to spend in Sleepy Hollow to experience everything it has to offer. Keep reading for the perfect itinerary for a spooky weekend in Sleepy Hollow!
Day 1: See the setting of the “Legend”
Stroll through Sleepy Hollow Cemetery
Start your first day in Sleepy Hollow by visiting the Sleepy Hollow Cemetery. Sleepy Hollow Cemetery is a beautiful and historic cemetery that should be on every Sleepy Hollow itinerary. The cemetery is the final resting place of many noteworthy individuals including Andrew Carnegie, Elizabeth Arden and Walter Chrysler. Notably, it is also the final resting place of Washington Irving, the author of “The Legend of Sleepy Hollow” and man ultimately responsible for stirring up worldwide interest in the small village.
There are several different tours of the cemetery offered during the fall season. It’s also easy enough to walk around on your own and take it in at your own pace. A few tips for visiting the cemetery:
- There is parking available inside the cemetery. If you enter through the South Gate (430 N Broadway) entrance, you can park along the side of the main street (parallel to the stream). Keep in mind the cemetery is only open until 4:30PM.
- The cemetery is very hilly so wear comfortable shoes and be prepared to walk up and down hills.
- Take “The Original Knickerbocker Tour” if you want to learn more about Washington Irving and see the inside of a crypt.
- If you walk to the Moller grave plot and look in the distance, you will see a church. If you continue looking in the distance beyond the church, you can see a faint outline of the New York City skyline!
Walk across the Cemetery Bridge
Unfortunately, you will not be able to see the Headless Horseman Bridge described in “The Legend of Sleepy Hollow” as it is long gone. However, you can visit the Sleepy Hollow Bridge (located just outside the South Gate of the cemetery) that spans the steam at the same spot as the former bridge. Additionally, inside the Cemetery, you can visit the Cemetery Bridge. The Cemetery Bridge spans the stream that runs parallel to the cemetery. Although the Cemetery Bridge is not the original Headless Horseman Bridge, it does have the same rustic look I would imagine the original bridge had. It’s also a great spot for a picture opportunity.
Explore the Old Dutch Church
While you are visiting the Sleepy Hollow Cemetery, you need to check out the Old Dutch Church and Burying Ground. The Old Dutch Church and Burying Ground is the church and churchyard featured in “The Legend of Sleepy Hollow.” The Old Dutch Church and Burying Ground is technically a separate entity from the Sleepy Hollow Cemetery. However, the Old Dutch Church is adjacent to the Sleepy Hollow Cemetery and shares an entrance with the Cemetery so it is essentially only one stop to visit both sites.
Grab lunch on Beekman
After working up an appetite walking around the cemetery, head to back into town for lunch. Beekman Street is one of the most popular streets in Sleepy Hollow and there are plenty of cute lunch options along this street.
Head to Irvington to learn about the Myths and Mysteries of the Octagon House
Just outside Sleepy Hollow, is the town of Irvington (named in honor of Washington Irving). The Armour-Stiner Octagon House is an extremely unique house. As you can probably guess… it is shaped like an octagon. It is the only known, fully domed octagonal residence. You can only view the house by booking a tour. The tour takes you through the first three floors of the house, but unfortunately does not go to the dome due to safety concerns. During the Halloween season, they offer Halloween themed tours. I did the “Myths and Mysteries of the Octagon House” tour which goes through the history and architecture of the house, but also highlights some of the supernatural myths and mysteries associated with the house.
Eat pizza in Tarrytown
Since the next stop is also in Irvington, I would find a dinner spot in Irvington or Tarrytown rather than driving back to Sleepy Hollow for dinner. During my visit, I stopped for dinner at Capri Pizza. The pizza was so yummy and the restaurant is just a five minute drive from the next stop!
See the “Legend” performed under the stars at Sunnyside
After dinner, the next stop on the Sleepy Hollow itinerary is Sunnyside. Sunnyside was the home of Washington Irving. It is located on the banks of the Hudson River and the backyard of the home has a beautiful view of the Hudson River lined by fall foliage. During the fall/Halloween season, Sunnyside hosts several special events. I would highly recommend attending the event, “Irving’s Legend,” where “The Legend of Sleepy Hollow” is performed on the grounds of Sunnyside at night under the stars. The Headless Horseman even makes an appearance! They also have fall themed beverages and snacks at the gift shop to sample while watching the show. If you like hard apple cider, make sure to try out the cider donut hard cider they sell at the show. This was one of my favorite experiences during my trip to Sleepy Hollow!
Day 2: Historic Homes and Jack O’Lanterns
See a show at the Tarrytown Music Hall
Day 2 of the Sleepy Hollow itinerary starts at Tarrytown Music Hall. Tarrytown Music Hall is the oldest theater in Westchester County. They put on several Halloween themed shows during the Halloween season. During my stay, I saw “Dracula and the Theatre of Doom,” which is described as “an interactive thrill ride that uses the entire Music Hall as its backdrop!” In this show, Dracula was on the loose in the Hall and we (the audience) moved between the different spaces of the theatre (from the stage, to the dressing room, to the basement and balcony) as the show progressed. I thought this was a funny and unique show and would recommend for a fun experience.
Explore Main Street in Tarrytown
Tarrytown Music Hall is located on Main Street in Tarrytown. The street is adorable and lined with hip shops and restaurants. After the show, stroll the street, grab lunch and explore some of the local shops.
See the unique stained glass windows at Union Church of Pocantico Hills
From the outside, the Union Church of Pocantico Hills is a small and unimpressive church. However, inside, you will see remarkable stained glass windows. The stained glass windows were commissioned by the Rockefeller family and created by master artists Marc Chagall and Henri Matisse. You need to purchase tickets for a short tour to see the inside of the church and the windows. I think the price of admission is worth it to see the windows, but be aware that they won’t let you take any pictures inside.
Visit the home of the richest American at Kykuit
Kykuit was the estate of John D Rockefeller and later home to four generations of Rockefellers. John D Rockefeller was the first American billionaire and is considered by many to be the richest American in history. The interior of the home was beautiful and opulent (as you can imagine with all that wealth). However, my favorite part was the front exterior, gardens and backyard that overlooked the Hudson. You can only see the home by booking a tour. The tours meet at the Phillipsburg Manor Visitor Center and then you take a shuttle up to Kykuit. I did the 1 hour highlights tour and felt that was sufficient to get a feel of the home.
See amazing pumpkin displays at the Jack O’Lantern Blaze
In the evening, head outside town to see the Great Jack O’Lantern Blaze in Croton-on-Hudson (about 20 minutes outside Sleepy Hollow). The Blaze is epic! It is a walkthrough experience featuring over 7,000 hand-carved pumpkins arranged in elaborate sculptures and displays. The Blaze is located on the grounds of the historic Van Cortlandt Manor. Some of my favorite displays include a Pumpkin Bridge, a tunnel made of pumpkins that changed colors as you walked through it, a spider web and spiders, a Statue of Liberty display and a Headless Horseman display.
The Blaze offers hot cocoa/cider and beer/wine/hard cider so you have something to sip on as you walk through the site. It took me about an hour to walk through, but you are able to walk through at your own pace so you can take as much or as little time as you want there. I can honestly say I’ve never seen anything like it!
**Pro tip** Tickets for events in Sleepy Hollow sell out extremely fast during the Halloween season so make sure to get your tickets in advance! I booked my tickets a month in advance and many events/times were already sold out.
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