The County That Chose Both Sides

Westchester County during the Revolution was one of the most politically divided places in colonial America, and I think that story is just as important as the battle itself — maybe more so.

People think of the Revolution as Americans versus British. In Westchester, it was neighbors versus neighbors, families split down the middle, farmers who had known each other for thirty years suddenly finding that one of them was supplying the Continental Army and the other was passing information to British foragers. The county's Loyalist population was substantial and, in many parts of the county, dominant. When the British controlled the area after White Plains, they were not occupying enemy territory — they were, in a meaningful sense, coming to the aid of people who had wanted them there.

What this means for how we understand White Plains is that the battle was a military event inside a much more complicated social and political situation. Washington's army was fighting through a county where a significant portion of the civilian population did not want them to win. The local militia who fought on Chatterton Hill were not representative of the county as a whole — they were the Patriots in a community that included many who were not.

The postwar settlement in Westchester was harsh. Loyalist properties were confiscated, families expelled, social networks dismantled. The men who had worked within the British system — some of whom had protected their neighbors and kept order better than the guerrilla war that preceded the British occupation — were treated as traitors by the victorious side. That's what losing a civil war looks like.

I spend a lot of time working with the county's Revolutionary-era records, and what strikes me most is how ordinary it all looks at the document level. Farm inventories. Property records. Church records. The war was fought over and around people who were trying to grow wheat and raise children and pay debts, and it disrupted all of that with a thoroughness that the subsequent mythology of patriotic sacrifice tends to obscure.

White Plains is remembered as a battle. In the county records, it looks more like a catastrophe that happened to people who had not asked for it and who survived it as best they could, regardless of which side they were on.