To my mind, it’s the perfect American Civil War border state story. Take a look at this 1970 aerial photo of Georgetown, DE’s Public Square and Circle. The two circled buildings are the Brick Hotel (bottom) and the site of the Eagle Hotel (right side).
“One local folk tale concerning the [Brick],” says its National Register of Historic Places application, “centers on its reputation as a favorite lounging spot for staunch supporters of the Union cause at a time when the county was leaning toward the Confederate cause in public opinion.

“The southern sympathizers in the area were in the habit of spending their evenings in the barroom of the Eagle Hotel elsewhere on the Public Square and Circle. Late in the evening when both sides had had their fill, tradition says that they piled out of their respective refuges and fought out their differences in the middle of the Circle.
“In view of the political climate in Sussex County during the Civil War the story is quite possibly true.”
During the Civil War Delaware was considered a Union state, though the truth on the ground was far more mixed. Imagine the Brick Hotel/Eagle Hotel story occurring in, say, Massachusetts, or Georgia. The fight scene in the circle would have happened only one time, not regularly, night after night. One side would have been killed, maimed, or run out of town.
The Confederate Monument in Georgetown, DE is the only one in the US that remembers Delawareans who fought for the south. It lists 95 names, though in fact 2,000 to 3,000 Delawareans are estimated to have joined the Confederate army.
And from the Union side Delaware sent 8 regiments (3,200 soldiers), a cavalry battalion (300-1,000 soldiers), and a battery (100 soldiers). So more Union soldiers than Confederate, but not by an overwhelming majority.

It might be easy in today’s political climate to dismiss the Delawareans who went south as traitors whose names should be erased from history. But we should remember that the Civil War often presented families with impossible choices.
Take the case of Juliette McLane Garesche, a Wilmington, DE native. Her father Louis McLane had served both as a US Senator from Delaware and a US Secretary of State. Her grandfather Allan McLane of Smyrna was a hero of the Revolutionary War. You’d think Juliette would have naturally been a solid supporter of the Union.
But she married Peter Bauduy Garesche long before war broke out. They appear to have had a solid marriage, one that produced four children. As the war grew near, Peter’s politics veered towards the Confederate cause. Was Juliette expected to leave her husband to remain loyal to the Union?