My Home Town

On this, my forty-third birthday, I thought I’d pay a small tribute to my roots and share Ossining, New York with you. I was born in nearby Sleepy Hollow (known then as North Tarrytown) in 1967 and lived in Ossining until I graduated high school. I then left for college in Pennsylvania and had a 15-year odyssey of homes before moving back to stay in 2000 after I met my wife. In that time, I lived in Philadelphia, College Park, Maryland, New Orleans, Boston, Northern New Jersey, and Rochester. And here I am, typing at my kitchen table 1 mile from the home where I was raised and half a mile from Ossining High. Here is a little bit about my home town. 

This is Saint Ann’s Church. I was baptized here, confirmed here, eulogized my father here, married here, and had three of my children baptized here as well. I graduated 8th grade from St. Ann’s school up the hill in 1981.

This is 32 Linden Avenue. I was here almost every day from the age of 6 months until the 3rd grade. My mother worked as an RN, and my babysitter lived here. She’s like a mother to me, and her 5 children are like siblings. I knew every nook and cranny of that old house. It went on the market earlier this year and I walked through for the first time in 33 years. It was a powerful experience. This house is the reason I love old homes, especially homes with porches. Back when that porch was enclosed by screens I read about 1000 Sgt Rock comic books sitting in it as the world went by, with the breeze blowing my cares away. 

This is the infamous Sing Sing Prison, the genesis of the phrase “up the river” from old gangster movies, as it is up the Hudson about 30 miles from Manhattan. It is still in operation, and the Hudson line of Metro-North runs right through it before stopping at the Ossining station. Surrounded by walls, of course- That looks really cool on Google Earth. 

This is Southside Market, on the corner of Spring Street and Lafayette, about a block away from Sing Sing. It used to be a little deli called Pindt’s. My friend’s Dad bought it in the early 80’s, renamed it Southside, and made it a thriving enterprise. I started out as a stockboy there in high school (rotate the stock. New stuff goes behind, older stuff up front) and worked counter in college. I remember the rush of the 11:30pm shift of prison guards coming in after getting off duty. They all seemed to want Italian Combos. 3 meats and 2 cheeses. Those guys were grouchy after a long shift with inmates. And hungry. Ralph, my friend’s Dad, was one of the best men I ever knew. We spent hours on end together in there, working and talking about life. I eulogized Ralph too.

This is downtown Ossining on Main Street (creative name huh). When I was a kid the area was derelict and blighted because all the commerce from that once bustling downtown migrated to the Arcadian shopping center. It has taken decades for the downtown to come back, but it is back and getting better.

This is my old home where I grew up. The original house (mostly on the left) was a 3 bedroom baby boom era ranch. My father made 3 additions to it.

I have posted previously about my old neighborhood, as well as the now semi famous (Thanks to Mad Men on AMC) Ossining reservoir.  

I love this place, and I chose to raise my family here. I love how my daughter has the local accent more each day. I love that we call hero sandwiches “wedges.” I love the Yin-Yang quality of Sing Sing prison on the River and Maryknoll Mission up on the Hill. I love that when I sell a home here I get a new neighbor. I love seeing the Hudson from the top of almost any hill here. It is a beautiful river town with a rich history, and I know it like the back of my hand. I’ll post more photos and history as time goes on, but I thought I’d walk down memory lane a bit here.