Sleepy Hollow is such a fun town to visit during the Halloween season! Sleepy Hollow is a small town in the Hudson Valley region of NY and is about 25 miles north of New York City. The town was made famous by Washington Irving’s “The Legend of Sleepy Hollow.” Not only has the story become a Halloween classic, but the town has also transformed into one of the top Halloween destinations to visit in the US. There is no shortage of fun Halloween activities in Sleepy Hollow – ghost tours, historic cemetery visits, haunted mansions and more! With so much to experience there, here are 5 things you need to put on your Sleepy Hollow Bucket List:
1. Visit the Home of the “Legend”
Sunnyside was the home of Washington Irving, who wrote “The Legend of Sleepy Hollow.” 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. While visiting this year, I attended their special event, “Irving’s Legend,” where “The Legend of Sleepy Hollow” was performed on the grounds of Sunnyside outside under the stars. The Headless Horseman even makes an appearance! This was one of my favorite experiences during my trip to Sleepy Hollow and I would highly recommend.
2. Take a Stroll through Sleepy Hollow Cemetery
Sleepy Hollow Cemetery is one of the most beautiful cemeteries I have seen. It should definitely be on every Sleepy Hollow bucket list. The cemetery is the final resting place for many notable people including Washington Irving, Andrew Carnegie, Elizabeth Arden and Walter Chrysler. 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. While there, also check out the Old Dutch Church and Burying Ground (church and churchyard featured in “The Legend of Sleepy Hollow”) and The Cemetery Bridge (located over the stream that runs parallel to the Cemetery).
3. See Some Amazing Pumpkin Displays at The Great Jack O’Lantern Blaze
The Great Jack O’Lantern 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 about 20 minutes outside of Sleepy Hollow on the grounds of the historic Van Cortlandt Manor in Croton-on-Hudson. Although it’s technically not in Sleepy Hollow, it still needs a place on your Sleepy Hollow Bucket List. 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!
4. Learn about the Myths and Mysteries of The Armour-Stiner Octagon House
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.
5. 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.
**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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