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Upstate New York: My Pain in the Ass (That I Secretly Love)

  • Writer: Caitlin Lewis
    Caitlin Lewis
  • Oct 31, 2025
  • 4 min read


I’m an Upstate New Yorker. Born and raised. I bolted out of here the second I could, swore I was never coming back, and yet… here I am. Back in my hometown. Where the weather is absolute dogshit, the people are a mix of stuck-up horse-money elites and “I’ll fight you in the in the parking lot” locals, and the taxes are so high you’d think I was paying for a personal butler to shovel my driveway. (Spoiler: I’m not. It’s me, in sweatpants, cursing at a snowblower.)


But somehow—I can’t imagine living anywhere else. Because where else can you roll into a Stewart’s half-hungover, grab a breakfast sandwich that tastes like pure salvation, and wash it down with coffee strong enough to restart your soul? Nowhere. That’s where.


The Ugly Truth


Let’s be real. Upstate life is a fucking disaster half the time.

  • The Winters. The snow isn’t “pretty.” The first snowfall. It’s a four-month long Hunger Games where your survival depends on whether your snowblower starts . By February, we’re all dead inside.

  • The Taxes. Honestly, I think I’m funding NASA with what I pay. Meanwhile, the pothole outside my house is big enough to host an Airbnb.

  • The People. Half are wearing Patagonia vests and talking about their horses. The other half are blasting Nickelback from a rusted-out pickup with no muffler. And we all meet at Stewart’s like it’s neutral territory.

  • Track Season. Track Season. You ever want to test your patience—and your will to live? Try finding parking on Broadway during Travers. Between the horn-honking, out-of-towners in Range Rovers, and the Adelphi valet blocking half the damn street, it’s pure chaos.Meanwhile, Broadway’s crawling with drunk ideas in big hats, girls wobbling in heels they can’t walk in, and guys yelling “let’s hit Caroline’s” like it’s a spiritual calling. And I am one ass grab away from punching a guy in salmon shorts and a Vineyard Vines polo. (Yes, that actually happened this year.)

  • The Housing. Bonacio is throwing up houses faster than I can shake a stick at, and prices are rising so high nobody’s gonna be able to afford to live here anymore. It’s like Monopoly, but instead of “Boardwalk” it’s “Some Two-Bedroom Townhouse With No Yard.” Locals are getting priced out of their own damn town.


It Used to Be Ours


Here’s the thing—this used to be a little quaint town when I was growing up. Everyone knew everyone. Broadway wasn’t just a catwalk for rich out-of-towners, it was our street. But now? It’s infiltrated by city people in floppy hats who act like Saratoga is their personal playground. Newsflash: it’s not yours. It’s ours. We’re just letting you stay here. So sip your $19 craft cocktail and enjoy your AirBnB, but remember—you’re in our town. Don’t get it twisted.

A Certain Flavor


And yes, we New Yorkers—especially upstaters—have a certain flavor. We’re honest, direct, and allergic to bullshit. If you’re fake as fuck, trust me, I’ll clock it in five seconds flat. You’re not from here. Around here, if someone doesn’t like you, they’ll tell you straight to your face.


The Stuff That Sucks You Back In


And yet… despite all the bullshit, this place hits different.

  • Stewart’s. It’s not just a gas station—it’s a religion. Where else can you grab milk, beer, lottery tickets, an ice cream cone, and unsolicited life advice from the cashier named Doris, all before 9 a.m.?

  • The Food. The real Saratoga isn’t about fancy small plates and cocktails with lavender foam — it’s about comfort food and character. The Comptons breakfast could cure any hangover known to man. Harveys Bar wings? Fornos in the off season.

  • Drinking Culture. Caroline Street after midnight is like stepping into a simulation where everyone has lost control of their lives.. You’ll wake up with glitter in your hair, chicken tenders in your bag, and zero memory of how you got home.

  • SPAC: Tailgating in the parking lots is like a Saratoga family reunion — you'll see everyone you know, their relatives, and even your old math teacher drunk. Soon, you're on the lawn, barefoot, with warm beer, singing to a band you don't like. If it's Dave Matthews weekend, it's a cultural event. The town shuts down as people in tie-dye grill sausages off pickup trucks like it's a national holiday.

  • The Seasons. Fall in Saratoga is magical. You’ll buy a $9 pumpkin spice latte just to hold it in a selfie while screaming at traffic on Route 50. And honestly? Worth it.


Living in Upstate NY is like dating someone toxic—you bitch about them constantly, but the second they text “you up?” (aka, first snow), you’re right back in their arms.


You swear you’re leaving… and then you see the sunset over Saratoga Lake, or the ducks at Congress Park start following you like you’re their cult leader, or you get handed that magical Stewart’s coffee + sandwich combo, and suddenly—you’re in love again.


This place is exhausting, overpriced, and colder than Satan’s ass crack in January. But it’s also home.


So yeah. Upstate New York: you’re a pain in my ass. But you’re my pain in the ass.

 
 
 

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