We finally made it to Sleepy Hollow this fall! This was another stop I wanted to check off my Halloween list and this year I was able to make time for it and on my birthday of all days. We were able to make a nice day trip out of it since it was only about an hour and a half away. For some reason, in the past I thought it was longer because anything ‘upstate’ seems like forever. In reality, this isn’t that much upstate of Manhattan. It was an easy drive up and back, especially if you’re able to avoid rush hours.

It’s a relatively small town so it’s very easy to see everything in a day. We got there around noon so we were able to explore a little bit of the cemetery, see the famous town sign for a quick pic, take a tour of Lyndhurst Mansion and walk the grounds before having dinner at Horsefeathers. The town is well decorated and very festive, being a popular tourist spot. I didn’t get to check out the shops on their main street because we arrived later in the day but because it’s so close, we plan on coming back again next year because it’s just such a beautiful and easily walkable town.

The iconic Sleepy Hollow sign is on the side of the road right next to Sleepy Hollow High School. It was easy to spot, and conveniently marked on Google maps as well. And because we went on a weekday, it was easy to find a quick spot to park, get out and take a quick pic. You don’t want to loiter too long since it is a school zone area. Weekends during October I’ve read can get pretty busy. This comes down to pros and cons of what you want to experience though. Weekends are busier so it may be harder to find a spot to park and have to wait your turn for things, but it’s also when they have more festivals and fun special Halloween events. If you walk a few blocks over from the sign, you’ll find the famous Beekman Ave, where there’s a big clock and the Jack Skellington looking pumpkin display decorated right at the intersection.

Drive a little further down the road and you’ll be at the Sleepy Hollow Cemetery. The Old Dutch Reformed Church is right out front with a couple of parking spots inside the entrance but you can drive alongside the one-way road and park on the right all along the cemetery if you can’t find a spot, as long as you follow all the marked signs and rules. We didn’t get to see inside the church this visit because it was closed albeit coming during visiting hours. Note that the bridge right outside the church is the official “Headless Horseman Bridge” - you literally drive on it to get to the cemetery - but it has since been replaced by a more modern looking construction. If you walk through the cemetery to the Old Style Horseman, you’ll find a more iconic, traditional looking wooden bridge the town installed to fit in with the legend of Sleepy Hollow better, to appease the tourists and makes for a better picture opportunity. It’s very pretty walking through the path to get there during this time, seeing all the beautiful fall colors and the stream that runs through it. I came at just the perfect time as the fall foliage in this area was reaching peak. Driving through the cemetery as we left was also a very pretty ride. I know, it seems weird to describe a cemetery as ‘pretty’ but there’s something hauntingly beautiful about the mausoleums and different tombstones, especially during this time as the colors change with the spooky season. Speaking of spooky season, the hubby noted there were a lot of Hot Topic looking girls also visiting during this time. I imagine the weekends are even more packed with tourists and Halloween fans. They have day and night tours for the cemetery but I wasn’t sure if I wanted to go on a long walking tour at this time but maybe next time, if the weather is comfortable, a night time tour might be nice to try. We actually got very lucky this visit and it was a pretty warm day and a cool evening. It was unusually warm for my birthday weekend this year.

After the cemetery, we headed to the Lyndhurst Mansion for a tour. It was either this or the Armour-Stiner Octagon house but the Octagon house sold out before I remembered to book it, and the Lyndhurst Mansion had a lot of good reviews and gave you access to the grounds after the tour for you to wander to your hearts content. If you’re a history or architectural/home interior design buff, I recommend the Lyndhurst Mansion as one of your stops. It goes through the history of its three owners, from William Paulding, to George Merritt to Jay Gould. They used to have a Halloween tour but our tour guide said people complained and preferred to learn more about the history of the mansion than ghost stories so they only offer the classic tours at this time. (Hopefully next visit, I can book the Octagon House’s Myth and Mysteries tour to fit in better with the spirit of the Halloween season.) The mansion was built and decorated in a gothic style. I found it beautiful to walk through as all its furnishings and decor looked so regal and grand. I’ve never seen any of the shows and movies that it’s been featured in but I can definitely see why they would choose this building for their sets. And the grounds are also equally beautiful and were decorated for Halloween in good fun. Our tour ended right before sunset and we walked out to this beautiful view overlooking the Hudson river. It felt like the perfect ending to the evening for my birthday. We took a moment to take it in before leaving to head back to town for dinner.

We went to Horsefeathers for dinner, which came highly recommended by a few friends, and reviews and blogs I read online. There is definitely a wait because it is a popular spot and the hostesses to seat you do work a little slow (we tried earlier in the day before the tour and again after the tour and both times, it took a bit of a wait before someone came out to greet us and gave us an estimate for our wait time), but once you’re in, the service inside is normal. The inside decor is really festive and cute, with writers on the wall like Mark Twain, Edgar Allen Poe and Washington Irving. The food though, for me, didn’t really live up to the hype. I was in the mood for fish and chips and the fish was a little too crispy and the chips were more like potato wedges than fries, which I would’ve preferred to pair better with the fish. The crabcake was good though. The hubby had ribs and they were fall off the bone good but a little too oversauced. I probably should have gotten a burger instead since that’s what they’re well known for but I wasn’t in the mood for a burger. There were a lot of other things on the menu so maybe I’ll give it another shot if we visit again. I probably should’ve tried a drink but I don’t really drink and I’m in prep mode for the NYC marathon so it wasn’t really a good idea anyway. Two other recommended restaurants I’m looking to try next time are The Bridgeview Tavern and The Hudson Farmer & The Fish. Hopefully they fare a little better. After dinner, we walked around the block a little to kill time and check out some decorations. The shops were all closed by this time but it was a beautiful cool night to just walk since we were waiting for rush hour to die down before heading home. I found Sleepy Hollow very charming and everyone very friendly and informative. Hopefully next Halloween season, I can experience a spookier tour and see more of the town. I missed the Headless Horseman statue but that just means I need to make another trip back, of course!