Where: Hudson Valley, New York
When: November 10, 1999 / May 23-26, 2014
With: School / Dave, Jennie & Ernie
The Hudson River is the 315-mile stream of water that cuts through the state of New York from the Adirondacks all the way down to New York City where it dumps out into the Atlantic Ocean. It was one of the first waterways explored by early settlers to America, and as such, the valley that surrounds the riverbed has a long and diverse history. From early Native Americans and headless horseman to military colleges and art museums to US presidents and modern day commuters, the Hudson Valley wears a lot of hats. As such, a couple trips to this area can barely scratch the surface of all there is to offer.
But I sure did try!
I came here once for a day trip in high school, but I'll pause on that until later in this post. The first time I truly got to explore the Valley was when I was invited to a wedding over Memorial Day weekend. This meant that minus the wedding, I had two full days of exploration of the area. And I can confirm, it was not nearly enough time.
Dave and I arrived by train on Friday night from New York City to the town of Peekskill, right on the banks of the river. We wouldn't have a car until the next day, so we explored the downtown on foot and enjoyed sunset views while having dinner and a beer. It didn't take long to decide this was a beautiful place.
When: November 10, 1999 / May 23-26, 2014
With: School / Dave, Jennie & Ernie
The Hudson River is the 315-mile stream of water that cuts through the state of New York from the Adirondacks all the way down to New York City where it dumps out into the Atlantic Ocean. It was one of the first waterways explored by early settlers to America, and as such, the valley that surrounds the riverbed has a long and diverse history. From early Native Americans and headless horseman to military colleges and art museums to US presidents and modern day commuters, the Hudson Valley wears a lot of hats. As such, a couple trips to this area can barely scratch the surface of all there is to offer.
But I sure did try!
I came here once for a day trip in high school, but I'll pause on that until later in this post. The first time I truly got to explore the Valley was when I was invited to a wedding over Memorial Day weekend. This meant that minus the wedding, I had two full days of exploration of the area. And I can confirm, it was not nearly enough time.
Dave and I arrived by train on Friday night from New York City to the town of Peekskill, right on the banks of the river. We wouldn't have a car until the next day, so we explored the downtown on foot and enjoyed sunset views while having dinner and a beer. It didn't take long to decide this was a beautiful place.
The next day, we got our car and headed off for exploration. The area is famous for the many wealthy American families that have called this place home, including the Rockefellers and the Vanderbilts. But one of the most famous residents of this region is none other than Franklin Delano Roosevelt, 32nd President of the United States. His home in Hyde Park has been made a National Historic Site that is open to explore.
Oh look! The Roosevelts are welcoming us to their home. How kind.
A very cool treat as it was Memorial Day weekend was that the massive green lawns on the estate had basically been turned into a temporary army base. Historic vehicles, weapons and relics from each of the major US wars were set up around the grounds for exploration. Volunteers in period dress answered questions and even did some weapons demonstrations. While we weren't going to have time to visit West Point, just a few miles from here, this was probably the next best thing we could have asked for in lieu of a visit.
One guy was doing a demo of a gun from World War II. While there were no bullets, I'm convinced I would have nailed a target.
Dave doing some enemy reconnaissance.
Then we went from World War II all the way back to the Revolutionary War. These guys were demonstrating an old cannon, and man, that boom was loud.
After our indoctrination into war relics, we followed the long tree-lined path up to Springwood Estate. I couldn't help but picture Roosevelt wheeling his way along this path and enjoying the quiet serenity.
Before reaching his home, we came upon the Roosevelts final resting place amidst Eleanor's beloved rose garden.
Eleanor's stables are out this way too.
Her horses won a fair share of ribbons.
From the gardens, a final pathway to the estate.
Upon first seeing the estate, I was surprised to see how cute it was! It was like Italian villa meets colonial America. I loved the sandy bricks, white accents and green shutters. It seemed so welcoming and homey, especially with the ivy crawling up its sides. I'd buy this house!
Inside the home, it has been kept the same as when FDR lived here. His living room looked so cozy, with his personal books and board games and lots of windows. Even his wheelchair is hanging out in the corner.
The various bedrooms of the estate.
The Roosevelts' bedroom, including the President's private phone line. Imagine the world issues discussed on this very telephone.
And speaking of where the magic happens, here is the President's home office.
While the inside of the estate was beautiful, Roosevelt didn't live in the Hudson Valley for the interior views. His favorite time was spent on his back veranda taking in the fresh air and epic landscape.
Also on the grounds of his estate is the FDR Presidential Library and Museum. In here, documents, artifacts and relics from the President's life were collected and put on display to show the story of his life and presidency. Of all the presidential libraries, this one was actually the first.
Some of the relics are even outside of the museum, including busts of Roosevelt and his World War II ally Winston Churchill.
There were also pieces of the Berlin Wall, cut into silhouettes of people and dedicated as sort of a full circle display of the true end of World War II and its resulting conflicts.
A very inspirational way to kick off our first full day in the Hudson Valley.
After that, it was time for some lunch. Despite the proximity of the Roosevelt home to the Culinary Institute of America (another main attraction of this area), school was out and we needed to find a place to eat. The Hudson Valley is filled with tiny little towns that feel like they haven't changed in a hundred years. I can't remember the name of the specific one we found, but there were tons of them along the drive.
After lunch, we decided to investigate another industry of the Hudson Valley: wine tasting! While it's not the best wine and not particularly well-known, vineyards are always a beautiful way to kill some time. This was Clinton Vineyards.
As the sun began to sink in the sky, we decided to take a small walk. Or should I say, we took a high walk, along a bridge that spans across the Hudson River, appropriately called the Walkway Over the Hudson. This 1.28 mile pedestrian walkway was originally built in 1889 as a rail bridge, but has since been converted into a "park".
The views over the river and valley could not be beat.
Looking south, you'd never know Manhattan is just down there.
A view of the Mid-Hudson bridge.
Don't. Look. Down. Yeesh.
Contemplating the meaning of life.
Reached the halfway point.
And we reached the other side. Woohoo!
With the last fading bits of sun, we tried to squeeze in one more estate. So we headed to the home of the Vanderbilts. While we were too late to tour the inside, we could still see the grounds.
This mansion is one of the oldest in the Hudson Valley, built in the late 1800s.
It sits on a bluff with clear views down to the Hudson River and the surrounding mountains. This was a pretty tough view to beat.
After the sun went down, we got one last look at the Mid-Hudson bridge before calling it a night.
The next day was the day of the wedding, so our explorations took a brief hiatus. But Dave still found us an old classic diner to have breakfast in.
The wedding was held at a beautiful castle by Tarrytown. So again, while we weren't technically sightseeing, it still felt like we were exploring the area.
And we met up with our friends Jennie and Ernie who'd join us for a bit on the last day of exploration.
Jennie and Ernie have two adorable pups named Evie and TyTy who they had brought with them. So the next day, we decided to explore one of the many state parks in this region and its countless trails. First things first, hydration.
Ok, now the pups are ready to go!
We found a trail in the Rockefeller State Park Reserve (while we didn't see the family estate, we still got a bit of Rockefeller in). The views weren't as epic here, but that was due to the massive amounts of trees surrounding us, which we did not complain about!
Family post-hike portrait.
After that, the pups needed to head home, and we had time for one more bit of sightseeing before heading out ourselves. So we closed by exploring one of the darker parts of the Hudson Valley: the inspiration for the short story The Legend of Sleepy Hollow.
This is where I turn back to the one time I had been to the Hudson Valley in high school. We were studying American literature in English class and had started learning about the writer Washington Irving. He lived in this area in the mid-1800s and it inspired many of his short stories, including Rip Van Winkle and The Legend of Sleepy Hollow.
While here in 1998, we visited his home, Sunnyside, kept as it was when the writer lived here in the latter years of his life from 1835-1859.
But let's be serious, the reason The Legend of Sleepy Hollow is so famous is not for the beauty of the area. It's for the creepiness of the headless horseman! A quick summary of the tale. It is set in Sleepy Hollow, NY in the late 1700s and follows a love triangle between nervous school teacher Ichabod Crane, the beautiful Katrina von Tassel who he wishes to marry and local jock Brom Bones.
At a fall party hosted by Katrina's father, Bones tells a spooky local legend about a Hessian soldier who lost his head from a stray cannonball during the Revolutionary War. Every night, the soldier rides around in search of his head, but he cannot cross the bridge alongside the Old Dutch Church or he'll disappear in a flash.
Later at the party, Ichabod asks Katrina to marry him, which she declines, and he rides home crestfallen and spooked by Bones' stories. He comes upon a silent rider and soon realizes that his head is not on his shoulders, but rather being held in his hands. Ichabod takes off for the bridge by the Old Dutch Church in hopes of saving himself, but to Ichabod's horror, the rider crosses the bridge and hurls his severed head at Ichabod. The next morning, Ichabod is gone and Bones is left to marry Katrina. But was it really the headless horseman who whisked Ichabod's spirit away or simply a jealous Bones who successfully drove the schoolteacher away?
With that, the starting point of famous sites related to this tale is the Old Dutch Church. In 1998, we got to go inside.
At a fall party hosted by Katrina's father, Bones tells a spooky local legend about a Hessian soldier who lost his head from a stray cannonball during the Revolutionary War. Every night, the soldier rides around in search of his head, but he cannot cross the bridge alongside the Old Dutch Church or he'll disappear in a flash.
Later at the party, Ichabod asks Katrina to marry him, which she declines, and he rides home crestfallen and spooked by Bones' stories. He comes upon a silent rider and soon realizes that his head is not on his shoulders, but rather being held in his hands. Ichabod takes off for the bridge by the Old Dutch Church in hopes of saving himself, but to Ichabod's horror, the rider crosses the bridge and hurls his severed head at Ichabod. The next morning, Ichabod is gone and Bones is left to marry Katrina. But was it really the headless horseman who whisked Ichabod's spirit away or simply a jealous Bones who successfully drove the schoolteacher away?
With that, the starting point of famous sites related to this tale is the Old Dutch Church. In 1998, we got to go inside.
In 2014, we stayed on the outside. Built in the late 1600s, this building is the second oldest church in the state of New York. It was fairly simple inside, but immaculately maintained in a way that doesn't give away how old it actually is.
Immediately alongside the church is a small graveyard. Of the notable burials in here are Catrina Ecker van Tessel, the possible inspiration for the story's Katrina, and Washington Irving's friend Samuel Young, a possible inspiration for Ichabod Crane.
Sitting on a much larger plot of land just behind the Old Dutch Church is the more famous Sleepy Hollow Cemetery. Many famous people came to call this their final resting place in a way that neatly wraps up our entire Hudson Valley weekend.
For starters, many of those famous families who had estates up and down the Valley are buried here, and their graves look more like their mansions than traditional tombstones. Famous families buried in here include the Astors, the Carnegies, and the Rockefellers.
This is also where several members of the American car families came to rest, including the Chryslers.
But of course, the most famous inhabitant of the Sleepy Hollow Cemetery is the writer of the story himself, Washington Irving.
But in 2014, we weren't leaving until we found a bridge. And while this may not be THE bridge, it looked pretty perfectly believable as the one the horseman should have disappeared into thin air on as he rode over it chasing down poor Ichabod Crane.
This is Dave's best reenactment of Ichabod. He absolutely loves this story.
And so, on both trips, with a tour of a graveyard, we packed up and headed back down south. I couldn't believe that after a long weekend (albeit, with a wedding in the middle), we felt like we had barely cracked the surface of activities here in the Hudson Valley. This is a beautiful corner of New York with something for everyone.












































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