Maryland surely must have one of the oddest shapes of all of our states. The ultra skinny panhandle and the split lower wing with a flared end can’t possibly be the way the state was originally planned. And, in fact, it wasn’t.
The royal charter described the northern border of Maryland as the 40th parallel, which should have been easy to settle because Pennsylvania’s southern border was also mandated as the 40th parallel. The problem was that the 40th parallel actually cut just north of Philadelphia which was at that time the capital city of Pennsylvania. This discrepancy was one of many examples of how hard it is to draw up borders sight unseen from across the ocean.
Pennsylvania wasn’t giving up Philadelphia, and Maryland was sticking to the border as dictated by the royal charter. The dispute took 100 years to resolve and led to a border conflict that was known as Cresap’s War. The intervention of King George II in 1738 finally re-located the Maryland/Pennsylvania border to 15 miles south of Philadelphia, which explains how Maryland was stuck with the thin little strip that stands today.