I finally went! Visiting Sleepy Hollow has always been a small dream of mine, how could it not be? It’s the Salem of New York. It’s kind of wild that it’s taken this long for me to actually visit. In any case, October is the perfect time to go. Fully recommend. Here’s how we (I went with my great friend Irene) spent the day!
We met at Grand Central and took a train up to Tarrytown (about $22/per person roundtrip, takes about 35 minutes from NYC). We thought about renting a car for the small trip, but it’s such a walkable area that I figured we’d be fine (I was right). From the Tarrytown train station we walked over to Pretty Funny Vintage, which sells antiques, gifts, souvenirs, jewelry, that sort of thing.
I didn’t realize how beautiful and old Tarrytown is. Look at the gorgeous the music hall.
We then headed to Sweet Grass Grill for lunch. The food was good yes, but the service was fantastic. The wait was on the longer side, but that only makes sense since it’s limited seating ‘cause… you know, the world is ending.
After food, we walked to Bella’s Boutique, which had great gifts and postcards for Sleepy Hollow. From there, we stopped into Tarrytown Pastry Chef because I’d heard good things about the Halloween themed cookies.
This was the point where we finally entered Sleepy Hollow. Look at this beautiful signage (below), it’s located on the corner of Broadway & Depeyster incase you’re looking for it when you’re in town.
We headed onward toward the Headless Horseman sculpture, bridge and monument.
After that we walked near Washington Irving’s grave, but I didn’t really have any urge in entering a cemetery to see a strange man’s grave. Seemed weird at the time and still does. But if that’s your sort of thing, many other people were doing just that. Then we walked through what once was old Sleepy Hollow Village (and is now just a residential street with a woody area) to get to the shoreline.
Once we got to the shoreline of the Hudson, it’s about a fifteen minute walk to reach the lighthouse (which is fully worth a view, who doesn’t love a lighthouse?) and there’s a lined, easy pathway to get there, too. The lighthouse was erected in the 1880s, which is incredible that it’s still standing, intact and beautiful as ever.
From here, it’s about a fifteen minute walk to get back to the Tarrytown train station. It was such a nice little day. There are other Halloween themed things to do nearby (The Great Jack O’Lantern Blaze, Home of the Legend, Philipsburg Manor), but they were either sold out or I’ve done them already, so it felt great to have a casual day roaming. It’s hard to find things to do right now (in the middle of a pandemic) that you can do safely, so it was great that this mini trip actually worked out. We spent 80% of the day outside and when we were indoors, nothing was crowded or felt unsafe in any way. If you’re ever in the New York area and you even kinda love Halloween, you should definitely make your way to Sleepy Hollow.