The Battle of Stow-on-the-Wold took place during the English Civil War. In the Spring of 1646, King Charles I of England was getting ever more desperate to hold the Royalist cause together whilst waiting for the long promised relief forces from Ireland, Scotland and France. Sir Jacob Astley took command of the Royalist forces in the west and began to gather up the remnants from the handful of Royalist garrisons still left in the west. As one could imagine at this point in the war, Royalist morale was pretty low. However, Astley, a stalwart of the Royalist commanders and an experienced soldier, was able to cobble together a force of 3,000.
The Roundhead forces (the Parliamentarians), who were slightly smaller, lined up to the northwest of Astley's position also along the current route of the A424. The Roundheads, flush with the confidence of an army on the brink of total victory, charged up the hill at the Royalist positions, near the present day Greenfield Farm. Initially, the Royalists held and even pushed the Parliamentary foot back. However, the Roundhead cavalry under Brereton rolled up the Royalist cavalry on the right flank. The Royalist cavalry fled the field and the infantry fought a running retreat southeasterly back to Stow Square.
Finally, Astley sat down on an ancient cross monument in the square and declared, "You have done your work, boys, and may go play, unless you will fall out among yourselves." This was a fitting end to the last major battle of the First Civil War from the man who was most quoted at the first major battle.