I’ve called Maryland home for decades — and yet it remains something of a mystery to me. I came here from Chicago, which may explain why some things have always felt slightly unfamiliar. From its flag to its roads, the state strikes me as a curious blend of contrasts and quirks — perhaps simply an enigma I’ve never been motivated to solve.
Take the Maryland flag, for example. To my eyes, it’s striking — but in a way that takes some getting used to. Yet Marylanders wave it with the enthusiasm of medieval standard-bearers. I’ve never seen a state flag flown so often. Maybe in Texas, but they were once an independent country. Perhaps it’s because Maryland’s flag features a traditional heraldic cross — more like a coat of arms than a typical state flag. I’ve never quite gotten used to it.
When it comes to driving and transportation, the quirks continue. On the highways, some drivers tend to linger in the left or middle lanes while others stop at intersections to wave you through — even when it’s not your turn, contrary to the rules of the road. It can be frustrating. And what about those highway exits on the left? That’s always felt backwards to me. Maybe these are all part of the Maryland rhythm.
Speaking of driving, getting to downtown Baltimore from the west can be tricky, since Interstate 70 was never extended into the city — a decision shaped by politics and community resistance. As a result, access from the west is indirect, making the route feel like a corn maze — just without the corn. Speaking of corn, as a Chicagoan, I can confidently say that Midwestern corn reigns supreme — sorry, Maryland.
When I first arrived, Baltimore struck me as a bit rough around the edges. There are certainly pockets of charm here, but they’re relatively small given Baltimore’s size. The area hospitals are excellent, but that feels like a baseline expectation for any major city.
History here is layered with irony as well. Maryland’s old state song rails against a “tyrant,” and while I first assumed King George, it actually refers to Abraham Lincoln. Perhaps that’s why, during the Civil War, Lincoln had artillery positioned facing Baltimore rather than toward the Confederacy. And despite being known as the “Free State,” Maryland allowed the ownership of slaves.
When it comes to leisure, Ocean City may be Maryland’s best-known beach, but there are plenty of other Eastern Seaboard beaches worth exploring. Yet for many Marylanders, Ocean City is the only beach that matters.
And then there are the local delicacies. I don’t like eating crabs, though crab cakes are delicious. I find the whole experience — cracking shells, working for a tiny morsel, getting my hands dirty with crab juices and Old Bay, sitting by a pile of leftovers — a little hard to enjoy. I prefer a Chicago Italian beef sandwich any day. You can find a Philly cheesesteak here, but aside from both being made of beef, they have little in common in appearance or taste.
A smaller population means fewer restaurants — and sometimes fewer options. But there are compensations. The trees here are abundant and beautiful. You’ll find actual forests around Baltimore, not just the “forest preserves” typical of Chicagoland (yes, that’s really how the locals describe the area). And to Baltimore’s credit, you can go from downtown to deep nature in less than half an hour, which is no small thing.
While tolls are a fact of life when driving, in Maryland, they generally fund the upkeep of a bridge or tunnel, which makes sense. In Chicago, toll roads seem ubiquitous and feel more like another general tax.
Baltimore’s suburbs lack the grid system found in Chicagoland, giving the roads a pleasantly irregular charm. In contrast, Chicago’s flat terrain makes it easy to lay out straight roads, so the only real challenge when driving there is dealing with traffic lights spaced about a half mile apart.
All told, Baltimore — with all its quirks and contradictions — has in many ways offered a better quality of life than Chicago, especially with its far more manageable winters.
— Todd Sulpar, Timonium
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