Sleepy Hollow Trip

I have been slacking with this blogging thing. With being a mom, wife and working full time, I just kind of let it go. But I want to make sure I update this with some fun posts and memories the kids can look back on. Our Sleepy Hollow trip was actually a month ago, but let’s see how much of it I can remember.


The village of Sleepy Hollow is about 30 miles north of New York City. It’s right near the Hudson River and is known to many via “The Legend of Sleepy Hollow” a short story written by Washington Irving. (He’s also buried there) They even made a movie about it starring Johnny Depp and Christina Ricci. You know, the spooky one with the headless horseman?

Every October, we have made it a family tradition to spend at least a weekend there. This year we booked a few extras attractions and even decided to drive up to Salem one of the days just to say we went there. Checked that off our bucket list. But to be honest, it wasn’t what I expected. I’ll get to that later. So we left on a chilly Friday afternoon. We were all so excited and had our things packed the night before. I made breakfast for everyone, and we double checked to make sure we got everything. Eric packed everything in the car, and I did some last minute cleaning. I hate coming back from a trip to a messy house. But then again, when you have little kids, it’s really difficult to keep your house clean.

It was around 1 o’clock when we finally hit the road. It took us about 3 hours to get there, but we were in no hurry and we love long family drives. We bought our road trip snacks, had Pandora set to oldies and then occasionally switched to country… we were just so excited to spend the weekend together in a different place, and stay at a hotel. We LOVE the excitement of staying over night in a hotel… 😂 When we arrived, we checked in, and unpacked all our belongings. For dinner our first night there, we went to this Mexican restaurant called Guadalajara Mexican Restaurant. We ate there last year, and their food was so good, we definitely wanted to go back this year. Best Mexican food ever.

By the time we were done, it was pretty dark out so we decided to go back to the hotel and hang out at the indoor pool before we went to our first attraction at 9 pm – The Great Jack O’lantern Blaze! This place is amazing. Volunteers carve thousands of pumpkins and set them up in these crazy beautiful displays. It was great going for a nice family stroll looking at all the pumpkin displays. It was definitely worth the $25 per person.

The next morning we woke up early, and Eric asked if I was sure I wanted to go to Salem. He really didn’t want to go but he would if I really wanted to. I mean yeah, we could have found some things to do during the day in Sleepy Hollow or the surrounding areas, but it was Halloween season, and I was about to cross over 2 new states I haven’t been to. So yeah, I said I wanted to go, but boy do I regret going. I loved the time we spent with each other and the experience of going to Salem. But the traffic was CRAZY and it seemed like there were more people there than New York City. We only spent about 2 hours there. We had another attraction to go to in Sleepy Hollow so we got in the car, and headed back. The traffic back was just as bad.

When we arrived back at the hotel, we had about 30 minutes to get ourselves put together from spending hours in the car. We were going to this murder mystery at this spooky looking mansion owned by Jay Gould. He was a leading railroad developer back in the 1800s and was super wealthy. This murder mystery was kid friendly and the kids loved it. It was a little silly but I loved hearing the kids laugh and get involved. After that was over we went back to the hotel and ordered some Italian food to our room. It took sooo long for the food to arrive, but the dessert we got was amazing!

This was our last night, and we were pretty ready to be back home in our own beds. We woke up the next morning, ate breakfast and did our usual cemetery walk. Sleepy Hollow cemetery is so beautiful, yet creepy. The morning was a bit chilly and the air was crisp – a perfect fall day. We didn’t spend too much time there. We decided we would just look for Andrew Carnegie and William Rockafellers final resting places and head home.

I planned on taking so many pictures during this trip, and in my mind I had every day and every activity planned out. It really didn’t go that way. We just kind winged it and enjoyed our time together. The Salem trip, where I imagined this enchanted Hocus Pocus land was just a stressful street fair type of walk. It was hot and crowded, and Carson wanted to be picked up every 5 minutes. I don’t know if we’ll be back to Salem anytime soon, but see you next October, Sleepy Hollow!