​Three Years In: Peekskill’s Slow Magic

The face that launched a thousand customers—Whiskey River’s smoked old fashioned savant and honorary Peekskill citizen.

As I turn a little over three years old in Peekskill, NY, I’ve noticed something odd: the town has grown on me like a second skin—or maybe more accurately, like a pair of slightly too-tight jeans that eventually learn your shape.

No, Peekskill isn’t love at first sight. It’s not Manhattan, which practically flirts with you from the moment you step off the train. Nor is it Madison, Wisconsin, with its lakes and liberal charm, or Sausalito, that jewel box of a town that glows like it knows it’s beautiful. Even Charleston wasn’t instant love. Back when I was in college, it wore a kind of sagging grace—tall houses listing slightly like they'd had one too many hurricanes, a downtown that looked permanently shuttered. These days, Charleston’s polished up. Sausalito chic. It could walk arm-in-arm down Fifth Avenue and not miss a beat.

Peekskill, on the other hand, hasn’t reached Rodeo Drive status. But it’s coming alive in its own way—like a teenager discovering vintage jeans and realizing she can start trends, not follow them. There's a hot foodie scene bubbling up. Taco District’s rooftop bar is a local star. Whiskey River serves burgers that could knock your cocks off (if you’ll pardon the anatomical drama). Even the appetizers change often, keeping diners on their toes like a good jazz solo.

But none of that would mean squat without the people. Always the people.

San Francisco pulled me in for 40 years not because of the hills or the bay or that famous bridge—but because of the friendships, the laughter in living rooms, the phone calls at midnight, the sense that I belonged. Peekskill’s starting to do that. Not by billboard or brochure, but through the quiet accumulation of connection.

To be perfectly honest, today’s journal isn’t going anywhere fast. My thoughts are scattered, and I’ve got an appointment looming that’s stealing away good writing time (nothing halts poetic flow quite like a calendar alert). Still, something sticks: there’s a kind of paradise quietly blooming here in Peekskill, made not from landscape or architecture, but from faces and voices I’ve come to know well.

And, by the way—it’s Thursday, though it really feels like Friday. I’m looking forward to the weekend, to slipping back into Manhattan’s embrace for a little while. Because even though I love Peekskill, New York is still New York. It doesn’t need people to sell its energy. It is the energy.

That’s the magic of smaller towns, though. They don’t flash—they whisper. And if you stay long enough, you learn to listen.

On North Division Street I met Suang and her dog Tish outside Whiskey River as they were studying the menu.