Welcome to the Neighborhood: Ossining, NY

In the name of small scale adventure, I’m spending one day each month exploring an area in or around New York City that I’ve never been to before. Welcome to the neighborhood. 

Visiting my hometown in December after I’d decided this year’s monthly challenge would be one of mini trips, I sat on the sofa with my mom Googling “interesting places around NY.” Because the challenge emphasizes new-to-me spots, that basically wipes out every Manhattan neighborhood as candidates. But, I wanted to think beyond deep Brooklyn so there I sat looking at neighborhoods across the outer boroughs and looking at towns in New Jersey, Long Island, “upstate” New York, and even as far as Connecticut. “Day trips” have range when you’re an early riser.

I found Ossining through a Reddit thread. A brief orientation from their town website: “On April 2, 1813, the Village of Ossining became the first incorporated village in Westchester County to be state-chartered. Today, Ossining is a culturally diverse, affordable place to live, rich in both history and natural beauty. Approximately 30,000 people reside in the three and one half square miles of this historic Village on the Hudson River.”

I thought I’d never heard of it until I placed it in further context—Ossining was previously called Sing Sing. In 1825, 12 years after it became an incorporated village, native granite was used to build the first cellblock on what would become Sing Sing Prison. From the town website, “Commerce and industry flourished throughout the 1800s. This industrial growth included a shoe factory and a stove foundry, both of which relied on convict labor. As the prison became notorious, the village tried to distance itself from the prison’s harsh reputation and changed its name to Ossining on March 25, 1901.”

Like most things with the U.S. prison system, the story is a little darker than a short paragraph on a town website can cover, so I turned next to the Sing Sing Prison Museum. It wasn’t just “native granite” being used to build the first cellblock, it was 100 incarcerated men using it. They’d been transported from Auburn Prison (NY) to Sing Sing and forced to excavate that marble from a nearby quarry, building their own cells. 

More from the Prison Museum: “The prevailing form of punishment at Sing Sing Prison followed the “Auburn System” in which the incarcerated were confined to solitary cells at night and worked silently in “congregant” labor groups during the day. This system, which also employed the “lockstep” as a method of controlling and moving inmates through the prison grounds, gradually became adopted as the primary system for prisons in the United States over the competing solitary confinement system used at Eastern State Penitentiary in Philadelphia. Sing Sing Prison was also the site of the infamous “Death House” where 614 executions (including 8 women) by electrocution took place between 1891 and 1963.” 

The site continues, “In the early 20th century, prison reform initiatives resulted in dramatic changes in the treatment of the incarcerated such as the abolition of the lockstep, the granting of “freedom of the yard” to inmates, and the introduction of baseball and other recreation.”

Sing Sing was most recently on my mind because of the 2023 movie of the same name. Sing Sing (the movie) focuses on a real program held at the prison called Rehabilitation Through the Arts (RTA). In the film, a newcomer joins the group and they decide to stage their first comedy show. It was met with incredible reviews when it came out, lauded for themes of humanity and purpose through theatre as well as connection, redemption, and the power of art. What I hadn’t realized before I sat down to watch was that much of the cast is RTA alumni. A really wonderful film all around and I’m grateful I took the time to watch and feel a little more connected to the place I would be visiting this month.

I’m jumping out of order here, but during my day in Ossining, I met a woman at the bookstore who had just planned an event there with Hudson Link for Higher Education in Prison. Hudson Link’s mission is to empower people and communities through college education, reentry support, and grassroots advocacy—transforming lives, families, and entire communities. I highly, highly recommend looking into the work of Hudson Link—they’re doing really amazing things and I feel grateful to have accidentally bumped into their story.

So that’s a little Ossining history. What does it look like to spend a day there? On a snowy Sunday morning, I left my apartment in Queens and walked to my favorite bus, taking it to the Metro North station. The train ride from Harlem-125 to Ossining was 52 minutes (and $11.75) making it a perfect day trip candidate. 

The train drops you off maybe a 5 – 10 minute walk from the main part of town. It’s hard to remember now how long that actually may have taken as, between the fresh snow and the steep hills, it was slow, cautious moving.

I’d done a little research into Ossining—and chatted to a friend who used to live there—which led to First Village Coffee. Like all the best cafes, First Village was more than just a place for a cup of joe. When you walk in, you’re greeted by a table of local crafts, art, and clothing all for sale. Then there’s the record player and the featured coffee roasters. (I got my brother a bag for his birthday.) The staff are welcoming and kind. I had a beet root latte and a vegan chocolate chip cookie ($12).

This is absolutely not the point, but I will always shout out a coffee shop that offers fun tea lattes that don’t have caffeine. A fun purple drink with a frothy white heart that won’t have me wired until 1:00 AM? Sign me up. And, as an active baker, I have high standards for my sweet treats. I’d eat those cookies ad nauseum. What I loved about First Village was that it immediately felt like a community space and not just because of the bulletin board with local happenings or the table games in the corner. It was just immediately obvious that this was a place people gathered. That people smiled at each other and connected. That will always be my favorite kind of place.

When I decided this year’s Monthly Challenge would be these day trips, I wasn’t sure how much I should plan and how much should be left to wandering. In this first go around, I landed somewhere in between. I had a few places I wanted to go, but I also wanted to be open to the unexpected. 

The next couple hours were spent putzing through the snow, chatting to locals, and reading all the “town history” signs along the street. We walked along the Old Croton Aqueduct Promenade and then kept going through a little park that was an absolute winter wonderland. We met a dog named Wesley, sliding through the snow in boots that surely were not his choice.

Because it was a Sunday in winter, there were a few things I knew I would be missing—the library and the Farmers Market mainly. Many folks mentioned the Farmers Market to me which used to run every Saturday in the town square but now skips some of the coldest months. Should I go back in the summer, I’d want to go on a Saturday to check out both these things.

One thing I was surprised to see closed was the Sing Sing Kill Greenway. Near the community center, there’s an amazing view of the Double Arch Bridge and a path that leads along the water. I assume a casualty of a snow day, so that’s another thing I’d definitely prioritize on a return trip. That said, for any architecture/infrastructure nerds, the Double Arch Bridge is a really neat piece of engineering.

Walking through the town is basically just small business after small business. Shops, restaurants, laundromats, bodegas. A random side quest took me to the grocery store to buy a very mediocre whole wheat roll from the bakery to eat plain as we went along. Silly as it sounds, there is something fun about not just doing the tourist-y thing, but also seeing what the day to day is. I’ll always say yes to stopping at the market.

For lunch, my friend had recommended Aji Limo, a Peruvian restaurant. I went for simple sides—tostones and avocado salad—and they were, as expected, great. (Another maybe $12 or so). Once again, everyone we were meeting in Ossining was warm and kind. I was soaking up small town charm just 50 minutes from the bustle of Manhattan.

The final stop of the day was Hudson Valley Books for Humanity. When I chose this challenge, I knew I’d be visiting a lot of bakeries and bookstores but I didn’t expect my first bookstore to be so, so special. 

Hudson Valley Books for Humanity sells new, pre-loved, rare and collectible books. But it’s so much more than a bookstore. It’s a true community space. Similarly to First Village Coffee, there are tables of arts and crafts from local creatives. Bookcase after bookcase of incredible reads. A record wall. A set up in the middle of the room for people to play chess (just ask for the timer)! Toward the back was a cozy couch, a little reading corner. I could have spent all day there. I left with two pre-loved essay collections ($15).

Overall, Ossining was a treat. I love a small town and a community space and being the first while chockfull of the second made it a really lovely time. I know my experience was colored with the magic of a big snowfall, but visiting on a wintry Sunday means I’ve only briefly pulled back the curtain on the town. Between the Farmer’s Market and the Greenway and, of course, the library, there would be much to explore on a return trip. There are many more restaurants and cafes still to try. And endless books to read. 

Welcome to the Neighborhood:

• January: Ossining, New York