(Originally posted on the website Heron Flight)

Of all days of this February, yesterday was perhaps the coldest and windiest day of all, the worst day to be strolling along the Hudson River. Not that we strolled much. We spent most of our time in the car. But the little bit that we spent outside walking was enough to turn our faces windburn red and make our little noses freeze. Yet, we ventured forth nonetheless. It was a day when the urge to explore was upon us. We could not be content to brave the day away basking in the warm glow of the dvd player. Hot cups of tea in stocking feet and brothy bowls of soup were not our course. We needed the satisfaction of adventure!

We went in search of Sing Sing. What better activity on a wind-worn day than seeking out one of America’s most notorious prisons? What better sight to warm the soul than that of “The Big House,” the house of murderers, rapists and other socially threatening individuals? With the breeze blowing fiercely south, we went “up the river”.

“Why?” you ask.

While in need of a destination, the idea of finding Sing Sing struck me as I did some reading for my current class. I’ve been studying deviance and have been required to read the book “Newjack” by Ted Conover, who purposely became a corrections officer at Sing Sing state prison in New York in order to write about prison culture. While checking a map yesterday to see exactly where Sing Sing was located, I noticed that it was just a few towns away from the legendary Sleep Hollow, the setting for Washington Irving’s famous story. It was there that the headless horseman haunted the dwellers of the riverside village. The combination of interest in Sing Sing and the curiosity of experiencing Sleepy Hollow was enough to impel Arissa and I to hop in the car and speed our way to New York in spite of the chilliness of the day.

Seventy-five miles later, we found ourselves on the Tappan Zee Bridge, spanning the churning brown waters of the Hudson River north of New York City. To our right, the George Washington Bridge crossed the same waters, the rising columns of Manhattan’s skyscrapers visible beyond its suspension cables. To our left, somewhere on the eastern bank upriver was Sing Sing.

Immediately after crossing the bridge, we exited the thruway to take Route 9 north. The first town we passed through was Tarrytown. There we were soon impressed with the stone church building of the First Baptist Church. Here we made our first exposure to the wind to take a few pictures of the church. We endured only long enough to click off a few shots and headed back to the car, happy for the shelter of my little Toyota.

Next we entered the village of Sleepy Hollow. I could see how this little town could be spooky as in the “Legend of Sleepy Hollow”. There was a cemetery there that stretched for nearly a mile along the main road. We came across a sign that signified the original location of the bridge over which the headless horseman traveled. I could just picture the fog coming off of the river, “spookyfying” the whole God-forsaken place.

A few more miles up the river, past Briar Cliff Manor, we arrived at Ossining, the home of Sing Sing. It wasn’t always called Ossining. Originally, it shared the same name as the prison, derived from the name of the Sint Sinck American Indians. Eventually, not wanting to be associated with the stigma of the prison, the town changed its name to Ossining. Construction of the original prison was begun in 1825. 100 inmates from Auburn prison arrived in that year to begin excavating marble from which to build their own cells. Each cell was only three feet, three inches wide, seven feet deep and six feet, seven inches high. Three and one half years after arriving, on November 26, 1828, the inmates were locked into the cells they had built. The next day, a Bible was provided for each of them. (Click here to read more about Sing Sing on Wikipedia.)

I have to say that Sing Sing prison is the best kept secret of any town in North America. There was not one sign anywhere in the town of Ossining that pointed us in the direction of the prison. When first entering the town, we thought, “It’s a maximum security prison. It must be pretty easy to see. Right?” Wrong! We drove through the town and back again without finding the prison! I remembered that Conover, in his book, mentioned that you could not even see the main gate of the prison from the town because originally they brought the prisoners to the prison by way of the river. The main gate faced the river. I remembered that he said that only a few sides of the high prison wall were visible from the town. Eventually, quite by accident, we came across these walls on State Street. The cold, windy climate of the day was a quite fitting setting for our first encounter with the wall. It was high and cold. No life passed through that wall. There was no escape from it. The whole prison sat below the edge of a hill along the river. Moving further uphill along a side street did not provide anymore of an expansive view of the prison complex. It was virtually cut off from the town proper, imprisoned between State Street and the cold rough waters of the Hudson.

We clicked off some photos after finding the prison walls, before noticing the signs that said “photography prohibited”. (I have since uploaded them to my website. Deviant? You know it!) Then we began looking for a place to eat dinner. We drove around Ossining, back and forth a few times. We discovered Main Street. Then guess what we found. Another entrance to Sing Sing! Off of Main Street, we went down Hunter Street and suddenly found ourselves in front of an employee parking garage! Straight ahead of us there was a guard tower visible behind razor wire. There was a sign that said “Visitor Parking.” We followed that driveway for a few dozen yards, just enough to click off another illegal photo of one of the brick prison buildings. Rather than come within sight of the armed tower guards again, we u-turned our way out of there and made for dinner once again.

I have to say that at the point of seeing the cold Sing Sing buildings, I felt completely disconnected from the atmosphere that Ted Conover described in his book. While he described situations in which correction officers sometimes had containers of urine thrown upon their faces, I sat in my car comfortably listening to classic rock on Q104.3. While he wrote of his continual fear that prisoners might become violent, and described how in his early days on the job he was once unexpectedly punched in the side of the head and nearly knocked unconscious, I held hands with my girlfriend just outside of the cement walls of Sing Sing. Even while stepping outside of the car to snap a photo, all was silent but the wind. We saw no sign of life whatsoever in the prison complex. It was an imaginary world that existed only in old movies and Conover’s book. Certainly, my comfortable, middle class, white New Jersey life had nothing in common with the harsh daily experience of the 2,000 plus inmates and the lesser number of officers responsible for their charge just beyond the wall in front of me. The wind effectively carried their voices of complaint, sorrow and turmoil out across the river yesterday. The prison was a ghost town, as far as I could tell.

We didn’t spend much time around the prison. Though my car is small, it is not inconspicuous, being RED! We figured it was best to high tail it out of there and make our escape back to “civilization”. Dinner had become a necessity.

Unable to find anything appealing in Ossining (while we enjoy Mexican food, we just weren’t in the mood to stop in any of the several restaurants that presented themselves), we turned our way south toward Sleepy Hollow in search of food once again. While the Headless Horsemen Diner was cute in a classic literary kind of way, it wasn’t all that appealing to our bellies in a satisfactory kind of way. We continued back down Route 9, eventually finding the Eldorado West Diner. Though you would think that “one could not go wrong with meatloaf,” you would be sadly mistaken in this case. When all else fails, resort to filling up on the complimentary breadsticks and crackers. Such was our dinner.

Soon thereafter, we raced our way across the Tappan Zee, through the crosswinds and the hauntings of Sleepy Hollow and Sing Sing, back to New Jersey, back to the comfort of the familiar. Ichabod be damned! We were home! Wind at our backs, prison behind us, we were home! The familiar and the comfortable.

CORRESPONDING PICTURE GALLERY:

• In Search of Sing Sing

FOR MORE PHOTOS OF SING SING BY A RETIRED SING SING CO:

• Sing Sing photos by Karl R. Josker