The Most Cheshirite People Not From Cheshire
- Richard Smith
- Jan 30
- 3 min read
Updated: Mar 11
A Richard Reggie Smith satire
Meet today’s featured Cheshirite couple—proudly, unmistakably, and hilariously not from Cheshire. He hails from Pepper Pike, Ohio. She’s from Oak Forest, Illinois. Somehow, through a mysterious combination of osmosis, Babel, and Facebook groups, they’ve learned to sound like locals… even if they still get almost everything wrong.
You will never spot them at Stop & Shop alongside the rest of us debating which rotisserie chicken looks least depressed. Grocery shopping just isn't them. DoorDash handles all life functions. In fact, the only time they set foot in a grocery store is during a snow panic—more on that later.
They believe a “packy run” is some sort of sack race at a church picnic. A grinder, in their minds, is either an exotic dancer or a questionable DJ name. Connecticut culture remains… a mystery to be unravailed.
Their dedication to fitting in, however, is impressive. Hidden away in a closet are three empty pizza boxes, carefully preserved for visiting family and friends. One from Pepe’s. One from Sally’s. One from Modern. When out of state relative's visit and pizza night arrives, Uber Eats quietly delivers pies from Fuoco Apizza, Rossini’s, and Vespucci’s, which are then secretly shuffled into the “correct” boxes. To any out of towner raised on Newman’s Own frozen pizza, it all tastes exactly the same anyway.
Winter, to them, is not a season—it’s a number. If it’s above 30 degrees, it’s officially shorts weather. Snow doesn’t count unless it hits at least two inches. A Connecticut winter feels like a mild fall back home. That said, the mere whisper of a “big whack” of snow sends them charging into the grocery store like it’s the apocalypse—grabbing milk and bread as if Noah himself is waiting outside. This is also the only time they do not use DoorDash, because how else can they report road and store conditions on The Real Cheshire Forum on Facebook?
Coffee culture? A mess. Cheshire Coffee must be an import company selling retail coffee beans. Main Street Caffe is a place to meet friends at, use the internet and get away from your kids and spouse. To them, Dunkin is a basketball move. Starbucks is the only acceptable coffee source, and yes, they pre-order and pay with Apple Pay. Naturally.
They are completely baffled when longtime residents quiz them on extinct landmarks—Cheshire Cinema, Farm Shop, Ray and Mary’s, Callahan’s, Waverly Inn, Damon’s, Friendly’s—as if this is some sort of oral exam required for citizenship. When someone explains the back way to avoid Route 10 traffic when CHS lets out, they stare back wide-eyed, like a child meeting Santa for the first time, because that is not the way Apple Maps tells them to go.
They have been spotted committing multiple local food crimes: once at Glenwood Drive-In, putting ice from their soda cups onto their lobster rolls “to cool them off,” the way they ate them back home. Another time at Blackie’s, they were observed boldly attempting to order
grilled turkey panini.
He coaches his 8-year-old son’s lacrosse team—not because he’s ever played, but because he looks exceptionally good in a coach’s outfit. She can often be seen on the bike trail, soaking in nature, staying fit, and fully immersed in her Apple Vision Pro—much to the horror of walkers, runners, and cyclists trying not to collide with her.
Weekends often include a three-hour session at C.J. Sparrow Pub & Eatery, listening to their favorite entertainer, Rickie Miller. Afterward, they Uber home because they shared a glass of beer. They don’t always drink—but when they do, it’s a 0.5% ABV Mexican-inspired beer called Cerveza Atletica.
They may not be from Cheshire. They may never fully understand Cheshire. But in their own strange, DoorDash-powered, Uber-
assisted way… they fit right in.
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