Check out a newer (2020) updated version of this post on my new blog: The Ultimate Guide To Sleep Hollow, New York
It’s officially the day after Labor Day and time to start planning those fall adventures! I know that I am. I’m a lover of fall and Halloween! Since I mentioned Sleepy Hollow, New York in my last post I thought I would start there. A few years ago, I ended up meeting my sister and brother-in-law in Sleepy Hollow because it was about the halfway point for each of us.
After a cursory search, I realized that Sleepy Hollow is a ‘sleepy’ small-town in the Hudson Valley, steeped in history and the Legend of the Headless Horseman and Ichabod Crane. I’ve always loved The Legend of Sleepy Hollow (book, movie adaptations and shows included). In case you are not familiar, Sleepy Hollow is the setting for Washington Irving’s The Legend of Sleepy Hollow.
Although it may be a small town they have capitalized on Irving’s success and there are quite a few things to do for those who love The Legend of Sleepy Hollow. Obviously, the best time of year to visit is October and the closer to Halloween the better!
I know at this point you think I’m that creepy person hanging out in cemeteries! I promise, I’m not. The Old Dutch Church and Burial Ground is the final resting place of Washington Irving (the writer of The Legend of Sleepy Hollow). But this cemetery has some impressive mausoleums and crypts and it’s worth a wander around, I promise!
There are Vanderbilts, Rockefellers, and even Van Tassels buried here!
The Philipsburg Manor is a living history museum where visitors can enter 1750. You can tour the manor house, explore the working gristmill, learn of the lives of the enslaved manor workers, visit the activity center and hear the history of the manor. It was also the inspiration behind the Van Tassel Manor in The Legend of Sleepy Hollow.
After visiting in October (2019) I wanted to let you know that the Philipsburg Manor is under construction. AND it’s also closed to tours on weekends in October when Horseman’s Hollow takes place. Horseman’s Hollow looks amazing and I’m already planning to come back and check it out next year! Be aware that according to the visitor center staff you need to buy tickets for Horseman’s Hollow months in advance!
This is one of the most popular sites in Sleepy Hollow, but many think it’s the original bridge. The bridge is over the river on the cemetery grounds and it can be found on the map available at the visitor center. While it is not the original bridge, it is something you should see.
If you drive the perfect speed over the bridge you can hear the hoofbeats of the Headless Horseman. The key is to not drive too slowly or quickly and it sounds like the Horseman is crossing the bridge. It’s pretty cool!
The sculpture of Irving’s Headless Horseman chasing Ichabod Crane is located outside of the visitor center/Philipsburg Manor. On my first visit, it took me around 10 minutes of driving around to find the sculpture. Around 10 years ago the village, formerly known as North Tarrytown, officially changed its name to Sleepy Hollow. The sculpture commemorates this event, is made of laser cut steel, and definitely something to see!
I recommend grabbing lunch or a drink at the Bridge View Tavern. It’s rated number 1 of 17 restaurant options in Sleepy Hollow by Trip Advisor this little place had some yummy food. I am admittedly easy to please when it comes to food and I can recommend the North American Elk Burger, the Chipotle Bison Burger, the Wild Boar Chorizo Burger, and the Disco is Dead fries (wild boar fries). Located at 226 BEEKMAN AVE, SLEEPY HOLLOW, NY 10591.
Expect a wait if you are visiting Bridge View Tavern/Sleepy Hollow on a weekend in October. I figured it would be smart to go at a “weird” time, around 2-2:30. But everyone else had the same idea and the wait for a party of 2 was around 45 minutes and a party of 5 was around an hour. Make the best of it and check out their Beer Garden (this was added since my last visit to Sleepy Hollow). I know it sounds super basic but try the Pumpkin Spice Sangria or a hot cider. I promise you won’t regret it! This place is worth the wait so grab and drink and enjoy the autumn sunshine until your table is ready!
Take a stroll and walk off lunch/dinner in Rockwood Hall State Park.
Sleepy Hollow Cemetery Tours: in Oct they host Edgar Allen Poe events as well as ghost stories by Washington Irving. They offer both day and night tours or you can do your own self guided tour. I caught the end of one of the actual tours and heard the tour guide saying that the price of your tour goes toward restoration efforts, which is a good enough reason to take the tour!
Irving’s ‘Legend’: Held at the Old Dutch Church and told by master storyteller Johnathan Kruk guests will get to hear a retelling of Irving’s The Legend of Sleepy Hollow.
Horseman’s Hollow: (Oct 4-6, 11-13, 18-20, 25-27, 31 and Nov 1-3). The haunts get historical at the Philipsburg Manor when you travel back in time to the cursed Sleepy Hollow. Watch out for the Hessian who is forever searching for his head!! I can’t wait to check this out! It’s recommended that you buy your tickets for Horseman’s Hollow a few months in advance.
The Great Jack O’ Lantern Blaze: Held at the Van Cortlandt Manor showcasing a stunning 7,000
Have you been to Sleepy Hollow? What did you think?
