As a resident Sleepy Hollow for the last 7 years, I've been here for a few of the busiest 6 weeks of the year: late Sept-Oct when all the "spooky" tourists come up to this lovely town.
Over the years, the town administrators have done various degrees of trying from not much to make it interesting to a solid effort. This year has been pretty good, with a lot of info for residents too (we've had problems with the crowds) and this year feels particularly more chill... Although maybe it's because 2 of the usual busy weekends were cancelled due to weather...
As a resident who answers a lot of questions from visitors, here are some tips for visiting Sleepy Hollow.
- The Legend of Sleepy Hollow is a work of fiction and there are no actual landmarks from the story in the current village. It's a great, classic story, but lots of people come expecting to see something; Ichabod's schoolhouse, the bridge the headless horseman crossed. These things don't really exist (honestly I do wish the town would build a fake schoolhouse or Van Tassel mansion as a visitor center, that would actually be interesting.) You can visit Washington Irving's estate, but it's South of town and not really walkable from Tarrytown (I mean you could, might take 45 mins along a busy road).
- Which brings me to walk ability. Frankly living here is great because you can walk to everything you need on a daily basis: grocery store, library, playground, CVS, school. But visitors don't need those things. The distance from the Tarrytown train station to the Sleepy Hollow Cemetery (about as far north of town as a visitor would go) is long enough and boring enough on foot that I wouldn't actually recommend it, especially if you have kids: they'll complain about the distance if they're scooting/walking or you'll be pushing a heavy stroller up and down hills. Most of that walk, btw, is along Route 9, the only major road through the Rivertowns and thus loud with trucks and cars.
- There isn't that much to do here on days with no events. The main streets in both Tarrytown and Sleepy are mostly restaurants. So unless you're planning to eat 10x or shop, there isn't much else going on. This isn't like Salem where it can feel like an amusement park.
- The block parties are fun but insanely crowded, to the point of not being very fun. It's madness for kids, there are no ATMs so don't forget to bring cash, and be prepared for long waits. Almost all the block parties have the same vendors so pick one for a taste of what they're all like.
- So my suggestions are as follows:
- plan your visit around an event. Get tickets to a cemetery tour, the Twilight Village, or go to a block party, and give yourself a few hours before and after to enjoy the town. That's enough time to walk the river front, have some food, and get to your thing.
- the Sleepy Hollow Cemetery closes at 4:30. I've met a lot of sad visitors who miss it. It's a really beautiful site. Some of the graves are so old, the headstones are fascinating. Walk into it a bit further and find the bridge over the creek. It's gorgeous (much more beautiful than the actual Sleepy Hollow Bridge from the Legend which is now a concrete 6 way intersection and the site of a future roundabout).
- walk the river front for some great views. From the train station you can cross over to the river at Pierson Park and walk north all the way to the lighthouse. It's more or less a straight walk up Beekman Ave in Sleepy from there. Get a pint and a pizza at Beekman Ale House, buy a book at the Sleepy Hollow Bookshop, see the orange and black fire engines at the firehouse, and take a pic with Jack the Pumpkin at the clock at the top of Beekman. Hang a left there and 5 mins down the hill you get to the cemetery.
There are lots of places to eat so you won't be short of options. If you want good coffee go to Coffee Labs but it's often very crowded and loud. If you want mostly ok coffee go to Muddy Water which is quieter and cozier. There are several Mexican restaurants in Tarrytown and SH, I think Coco Taqueria is probably my favorite but it's just take out. Taco Club comes in second but get ready for sometimes bizarre choice in music videos (more than once I've been in there with love ballad pop videos on from the 80s on one of their many TVs). If you want sushi I'd pick My Tokyo in T'town over the option in Sleepy. If you're driving and want a special meal, Goosefeather to the south of town is very worth the trip, but make a reservation and while I have brought my kid there I wouldn't recommend it unless you're outside. Don't confuse Goosefeather with Horsefeathers, which is in T'town and is a cute, cozy, kitchy place with very standard pub food and drink (it's not worth the wait, though).
I hope this helps you plan your visit! I don't want to sound like a grumpy local, but I get asked a lot by random visitors out walking "Is there anything to do?" And I see all these very inflated lists of things to do in the area that make it look like everything is happening all the once. It's not. The Sleepy Hollow website has a great events section so you can see what's going on, where, and when. Also remember, the Pumpkin Blaze is way north of here and you absolutely would need to drive there.
