Roundway Down may have one the most dramatic geographical features of any battleground, bar the cliffs at Pont du Hoc on the Normandy coast. The escarpment that falls away from the back of Roundway Hill is a sheer drop off and was the scene of a desperate retreat that ended with many cavalrymen going over the cliff.

After the stalemate at Lansdowne Hill a few days earlier, Waller wanted a decisive engagement with the Royalists that were working the area, so he set siege on Devizes in Wiltshire. Royalist Hopton, who had been injured in an accidental gunpowder explosion after the Lansdown Hill battle, knew he needed help, so he sent Prince Maurice on a end run to Oxford to get more forces to come to his aid. Those forces, under Lord Wilmot and Sir John Byron, approached from Oxford and Waller met them on the sweeping expanse of Roundway Down with a numerically superior force. Waller had what he wanted.