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My Westchester: A Journey Through The Decades

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I have lived in Westchester on and off for 40 years, and I’ve written about life here for more than a decade. But it turns out to be surprisingly hard for me to gather my feelings about this county in a neat little package under the heading of “My Westchester.” My Westchester is not a stationary, unchanging thing—it is a moving target, a complicated journey that has zigzagged up and down the Saw Mill Parkway for more than four decades.

In a misguided stab at upward mobility, my parents fled the Bronx when I was in middle school. They assumed that crossing the border into Yonkers would give us a picket-fence lifestyle, magically turning me into an accomplished and sun-kissed suburban teenager. Instead, my Westchester involved hanging out in sketchy parking lots and smoking Newport Lights with other underachievers in the girls’ room of a sub-standard high school. My life was entirely non-suburban: I wore excessive amounts of cheap eyeliner, I failed chemistry, and my first boyfriend went to prison for stealing a car. I too would head “upstate,” but in my case it was voluntary; instead of jail, I landed in a surprisingly decent state university. 

Susan Goldberg is a writer and editor whose work has appeared in the New York Times, Westchester Magazine, Working Mother, and many other publications. She has been a columnist for newspapers and online magazines and currently works as a college essay consultant.

 It never occurred to me to return to Westchester after college; I moved to Manhattan, reasonably sure I would never again venture north of 92nd Street. But marriage and impending motherhood changed my mind; I had developed adult onset suburban fever, a condition that is characterized by an intractable yearning for greenery, mudrooms, and quality school districts. 

We bought a fixer-upper in Chappaqua and hurled ourselves into a traditional Northern Westchester lifestyle: two kids, a porch swing, and back-to-back Labrador retrievers. For more than 20 years this was my Westchester, and despite a thin veneer of leftover city cynicism, I loved it all—the cozy sense of community and being “snack mom” for soccer; the four-burner Weber grill, and carpooling to bat mitzvahs. I loved my hydrangeas and the Bad News Bears ineptitude of my daughter’s third-grade softball team. 

But my kids are grown now, and I’m paying crippling taxes on a big, empty house. Even worse, I am right on the brink of becoming my neighborhood’s “Old Witch,” the scowling AARP biddy who glares at young moms in yoga pants—the ones who park their Escalades on both sides of the street while they wait for the school bus. I am feeling aged-out of Chappaqua, but the thought of returning to Manhattan is not as tempting as I thought it would be. (It seems I have lost my taste for studio apartments and $24 pork belly appetizers.) Westchester turns out to be embedded in my bones, along with my rapidly diminishing reserves of calcium. 

So I will probably stay in the county, following other empty nesters to a nearby condo community. I am thinking of an efficiently streamlined townhouse, where I can stay in touch with local friends, while letting go of my outdated ties to the PTA and travel soccer. In the next phase of “My Westchester,” life will imitate real estate—and both will be semi-attached. 

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We’d love to publish your essays (maximum 500 words) about life in Westchester. Email them to: edit@westchestermagazine.com

Subject line: My Westchester. All submissions become the property of Westchester Magazine. If published, they may be edited for clarity and space.

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