When the Civil War broke out in 1861, the majority of Newtown's young men joined Confederate forces. During the war, the town was "between the lines", nominally controlled by the Union but with much Confederate partisan activity. On May 24, 1862, Stonewall Jackson's Confederate forces advanced northward on the Valley Pike and attacked Union troops. At Newtown, General George Henry Gordon of the Second Massachusetts Infantry ordered his Federal troops to make a stand. The skirmishing involved heavy artillery fire, but Gordon's men retreated without loss of the important supply wagons. When Gordon left the town to Jackson's forces, both sides claimed a victory.