Let me start by saying that this New England trip was a trip of dreams for me. I’d been talking about going up there and taking a Halloween themed vacation in the origins of America for years and years, so for it to finally happen was, like I said, a dream come true. Everything about New England exceeded my expectations! I loved it all with every fiber of my being and would honestly go back to any single one of the seven states we visited in the nine days we were up there. A single day in each state (minus Massachusetts) was obviously not nearly enough, but we made the most of it and I’m beyond thrilled to finally be able to share with you all that we did, one day at a time!
Nancy, Melissa, and I flew directly from Lambert St. Louis International Airport to LaGuardia International Airport in New York City where our friends Charles and Kamber, who had arrived in New York City much earlier, picked us up in the rental minivan we would be traveling in for the next nine days. This beautiful Chrysler Pacifica was our home away from home throughout our time there.
SIDE NOTE: Mine and Melissa’s flights were literally “free!” With my Southwest Airlines Chase Visa, I had more than enough points to cover my roundtrip airfare and because of the promotion when I opened my credit card, I have a Companion Pass that allows Melissa to go anywhere I go for absolutely free! If you travel often, like I do, then you should seriously look into getting a credit card that rewards you with miles, so you too can travel about the country for next to nothing! I used quotes around the word “free” earlier because I obviously spent some money on this card to earn those miles, but I was going to be making those purchases whether I earned those miles or not, so why not get a card that allows me to do what I love to do for significantly less?
ANYWAY, the drive north to Sleepy Hollow was only about forty-five minutes because we were blessed with hardly any traffic leaving out of New York City. We were hoping the leaves would be more colorful as they were all still fairly green, but we got our wish by the time we made it to Vermont on Day Six, so that’ll give all you Leaf Peepers something to look forward to in this series!
In the months leading up to this vacation I was shocked by how many people told me they didn’t think Sleepy Hollow was an actual town! Nearly everyone had heard of The Legend of Sleepy Hollow, a story written and made famous by Washington Irving and sensationalized over the past two hundred years since its original publication back in 1820 by various prints, films, animated shorts, and television series, but nonetheless, I was blown away by the overwhelming number of you all that told me they didn’t think it was an actual place one could go visit, or hell, even live! So, for all those shocked to learn of its actuality, this should be quite a collection of photos for you because as you’re about to see, Sleepy Hollow, New York was the PERFECT beginning to our spooky and spectacular New England vacation…
I decided I would take a photo of me in every restroom I used on this trip. Anyone who knows me knows this could EASILY be its own series because I be using those restrooms all. day. long.
This was where we had our first meal. It was super old and adorable and the food was totally fine. Everyone working there was extremely nice, which we found to be the case absolutely everywhere we went! Regrettably, I was so hungry, I forgot to photograph my food, but as I’m no foodie, this was more or less par for the course.
They were renovating the riverwalk, which was a bit of a downer for us, but those renovations coupled with the haze just gave us another reason to return one day in the not-so-distant future. The view we were able to see was breathtaking, so I cannot wait to go back on a clear day when the work on the riverfront has been finished!
The Headless Horseman Monument! I was SO EXCITED to see this! The 1999 Tim Burton masterpiece, “Sleepy Hollow,” is one of my favorite films of ALL time, so I was PUMPED to see any and all the Headless Horseman stuff I could!
Charles embodying the spirit of the Headless Horseman!
As you can see, The Headless Horseman Bridge has been a bit modernized since 1820 when it was written about and featured in Washington Irving’s story.
Like Pocahontas and Grandmother Willow, Melissa too loves herself a good Weeping Willow Tree! I find them to be mystical and enchanting and I too love them so much, there were plenty around Sleepy Hollow, which really added to the incredible ambiance of the area.
The Headless Horseman Statue! Again, I was so beyond excited to be there at the time. I cannot express enough to each of you just how much of a dream come true this was for me.
Philipsburg Manor is a traditional 1700’s trading center and colonial manor that features a number of exhibits and hands-on demonstrations recreating that era. Unfortunately, we arrived too late to experience any of that, but still, we were able to take some incredible photos from the far side of this pedestrian bridge.
Again, another reason to return since we didn’t get the opportunity to experience this amazing looking place on this trip.
From Left: Charles, Kamber, Melissa, Nancy, and myself. Can’t wait to see where we’ll all go next October since New England was our second October Friendship Trip after Disney World last year!
This place just screams Halloween!
This was Downtown Terrytown. Terrytown and Sleepy Hollow were like Glen Carbon and Edwardsville in Illinois or Murrieta and Temecula in California, (there, I think I covered the majority of my audience with these examples of proximity). You didn’t really know where town began and the other ended (unless you lived there). It all combined seamlessly to give it a perfect small town Halloween feel.
Another restroom selfie this time in Coffee Labs Roasters Inc. in downtown Tarrytown! This coffee shop was phenomenal!
Loved their decor! This place just made me so damn happy.
This was Kamber’s coffee (I always get mine iced) and we thought it was just the cutest! Also, we got there right before closing time and they started playing the song, “Closing Time” by Semisonic and I absolutely loved that touch! The staff was super cool and I’d highly recommend going if the chance ever presents itself to you.
The Sheep Queen of Illinois, Nancy, was unavailable to be photographed with one of her many subjects due to us being in two different places downtown during the time of this picture.
Love me a good mural! Glad this one was made in time for our arrival!
Christopher Columbus was a rapist, pirate, and pillager, but because Halloween is all about horror, I thought I’d take a photograph of one of history’s leading villains. I absolutely love seeing his “day” being replaced by Indigenous People!
A cutie behind the stone wall.
This sign was cute, but the one you’re about to see is the real reason we stopped…
THIS was the sign we stopped for! Again, give me ALL the Sleepy Hollow!
I just thought this church looked cute and spooky at night. Gave me some gothic demonic vibes.
This park was enchanting. Not sure if it was technically in Terrytown or Sleepy Hollow as it was where both “welcome to” signs were located, but either way, we loved it!
Sleepy Hollow Cemetery is not only the oldest cemetery in New York state, but also has the oldest still practicing church in the state. Like a fool, I failed to capture a solid picture of this incredibly historic house of worship. I’m genuinely shocked and ashamed at this blunder.
So many of these graves were older than the entire state of Illinois! It was mesmerizing!
The figure at the gate sent chills down my spine even though I know they were the person there checking tickets to make sure you were actually supposed to be here, but I love a good silhouette!
Our incredibly knowledgeable tour guide and the lanterns we were each about to get.
I genuinely don’t know what my phone captured up on those steps. I thought maybe it was the tour guide, but I don’t recall a time I was ever that far away from him at any point because I wanted all the information, so you decide, did I catch a spirit?
There was quite a bit of old money in this cemetery. It truly boasted a who’s who list of the dead including many Rockefeller’s, Chrysler’s, and even Elizabeth Arden herself!
A shot of Rockefeller’s Mausoleum. We were informed that its larger than most apartments in New York City and after seeing it in person, I don’t doubt that fact for a second.
This was someone’s mausoleum and again, my phone captured something crazy with the light on the right.
A tour by lantern light is the only way to see a graveyard at night. I was loving every second of it!
The blue light in the sky is from the beautifully blue lit bridge that was down the hillside and over the river. I failed to capture a photo of it, but we did end up driving over it later that evening on our way to dinner.
They provide these tours from April through November and if you ever find yourself in Sleepy Hollow I would VERY MUCH recommend taking one. We took the one called “Aristocrats,” but there are a handful to choose from. Ours primarily focused on the aristocracy buried in the cemetery.
Some of these grave monuments were so elaborate. I just loved everything about this cemetery!
Random grave shot.
This was my favorite Mausoleum because it was so gothic looking. Give me all the iron gates.
Me trying to emulate the groundskeeper from The Haunted Mansion ride in Disneyland park!
We finished our evening in a city across the river, Nyack, and it too was absolutely outstanding! We had some delicious pizza here at this quaint pizzeria where – incredibly enough for Melissa – had a picture on the wall of the owner with the Backstreet Boys! Melissa LOVES the Backstreet Boys, so winding up in this place was pretty much fate for her!
Well, there you have it, our day in Terrytown and Sleepy Hollow! I do hope you enjoyed looking at these pictures as much as I LOVED taking them! I’ll be back very, very soon with Day Two where we traveled to Connecticut and got a lil’ physical before taking an even creepier ghost tour, but until then, I wish you all, all the best!
More haunts and happenings from our New England vacation:
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Great photos! I’m not sure what you captured on camera on those steps but it gave me the chills! I love that you guys went to the actual Sleepy Hollow, looks like a beautiful town. I also loved your Haunted Mansion picture. Can’t wait to see the rest of the pictures from the trip, especially that red coat!
Thank you & I’m not sure what’s in that photo either! I wish I knew! Sleepy Hollow was THE BEST! I cannot wait to share the next ones! I just haven’t the time, but they’re coming!
What a neat place to visit! I have an airlines credit card as well and it really does make a difference on bringing down the cost of your trip! Definitely helpful when paying for a family of five! Glad you all had a great time and I cannot wait to see more photos from more days!
My family of two benefits exponentially from this credit card, so I bet you’re super loving the card with a family of five! I’m looking forward to sharing more photos! I just seem to be having trouble finding the time! They’re on their way though!
I’d be one that didn’t know it was a real place! Always thought it was a myth nice set of photos. Looks like fun.
Thank you! We definitely had THE BEST time throughout our entire vacation!
Great photos! I’m not sure what you captured on camera on those steps but it gave me the chills! I love that you guys went to the actual Sleepy Hollow, looks like a beautiful town. I also loved your Haunted Mansion picture. Can’t wait to see the rest of the pictures from the trip, especially that red coat!
Thank you & I’m not sure what’s in that photo either! I wish I knew! Sleepy Hollow was THE BEST! I cannot wait to share the next ones! I just haven’t the time, but they’re coming!
What a neat place to visit! I have an airlines credit card as well and it really does make a difference on bringing down the cost of your trip! Definitely helpful when paying for a family of five! Glad you all had a great time and I cannot wait to see more photos from more days!
My family of two benefits exponentially from this credit card, so I bet you’re super loving the card with a family of five! I’m looking forward to sharing more photos! I just seem to be having trouble finding the time! They’re on their way though!