How to Spend the Perfect Fall Day in Sleepy Hollow
Fall in the Northeast is one of the most beautiful times of the year, and you’re probably thinking of places in New England like Vermont or New Hampshire. Did you know though, that Upstate New York has some great fall gems also? Last year, I made it a point to see more of my home state throughout the seasons. One of the popular fall towns to visit is Sleepy Hollow, in Westchester. As it’s the setting of Washington Irving’s “The Legend of Sleepy Hollow,” Sleepy Hollow has attracted lots of visitors at Halloween time. I don’t celebrate the holiday, but there’s still lots to do as it’s also quite scenic during the fall time. Here’s how to spend the perfect fall day in Sleepy Hollow, New York.
How to Get There
Sleepy Hollow is actually quite accessible from NYC. You can take the Metro North from Grand Central to Philipse Manor Station. The ride is just under 40 minutes. The drive is also not long (36 miles), just a little over an hour from Brooklyn without traffic. Due to the busy season though, you may have trouble finding street parking right away.
Sleepy Hollow is a small village, so you can easily head down south to Tarrytown in the same day. If you’re driving, it’s only a 5 minute distance and about 20 minutes in foot. I prefer to drive though, just to maximize my time in the area.
What to Do
Snap a picture to commemorate your visit at the Welcome to Sleepy Hollow sign on Broadway. It’s just by Sleepy Hollow High School, so you can’t miss it. Afterwards, walk over to Beekman Ave to explore the rest of the town. Beekman Ave is mainly known for its over the top Halloween decor, but there are a few shops or restaurants to stop in for lunch.
Headless Horseman Statue – This is just one of those tourist-y things to do. There’s nothing else here but it’s still one of the most visited photo spots in Sleepy Hollow. It’s an 18 foot sculpture of the Headless Horseman chasing Ichabod Crane, and it’s actually just near the bridge where the Horseman throws his pumpkin at Ichabod in the Legend of Sleepy Hollow.
Sleepy Hollow Cemetery and Old Dutch Church – Take a daytime walk of the cemetery where several famous figures are buried, like Washington Irving and Andrew Carnegie. Then check out the adjacent Old Dutch Church, where the legend is set.
Philipsburg Manor – A National Historical Landmark, Philipsburg Manor was an 18th century miling and trading complex that also held more than 20 African slaves. It currently runs as a non-profit museum. You can get a full view of the manor from across the lake at the Visitor Center parking lot.
Kykuit, the Rockefeller Estate – possibly my favorite place to visit in Sleepy Hollow, especially in the fall. Another historic landmark, Kykuit is a Gilded Age, 40 room mansion that was home to four generations of the Rockefeller family. The grounds are now open for guided tours only, where you can see most rooms of the mansion as well as all the artwork and gardens. Because you can only visit Kykuit on a guided tour, make sure to book your tickets in advance, as they do sell out, especially during the busy fall season. There are different times available, with tours ranging from 1.5 hours to the more in depth 3 hour tour. No photography/video is allowed indoors, but trust me, the mansion is absolutely stunning. If you’ve been to the Newport Mansions in Rhode Island, I’d say Kykuit is just as comparable.
At the outside grounds, you get stunning views of the Hudson as well as beautiful terraces and sculptures. I suggest going on the 3:45pm tour, as it ends around sunset, and the lighting just adds to the beauty of this place. I’ll just let these photos speak for themselves. (The tours leave on a bus from the visitor center at Philipsburg Manor. Do not type in Kykuit on your GPS as it will lead you directly to the estate and you won’t be allowed in).
Book tickets for Kykuit here: Kykuit, the Rockefeller Estate Tours
Sleepy Hollow Souvenirs – 80 S Broadway. Tarrytown, NY. A popular two-story souvenir shop in town where you can get all the Headless Horseman themed souvenirs as well as copies of the actual book. There are also lots of antiques and cute knickknacks to check out.
Westchester Riverwalk – Located in Tarrytown, walk down the riverwalk where you can see the Sleepy Hollow Lighthouse and the Cuomo Bridge. You can also see a bit of the NYC skyline in the far distance. There’s also a pumpkin arch up this season that makes for a cute photo op and it frames the bridge perfectly.
Armour-Stiner Octagon House – Located just 10 minutes south of Sleepy Hollow in Irvington, the Armour-Stiner House is another landmark worth checking out for its unique structure. It’s currently the only octagonal home in the world. A one hour guided tour will teach you all about how New Yorkers lived in this area during the Gilded Age as well as give some insight into the family that lived here as well.
Book your tickets here: Armour-Stiner Guided Tours
