The Romans occupied Weston from the 2nd Century AD, a date based on coins and pottery found in the village. Their Ryknild Street (now called Buckle Street) forms the parish boundary with Saintbury and provided a link with Watling Street and The Fosse Way. Weston, said to have been a station for the Imperial Post, lies roughly halfway between Alcester and Slaughter Bridge, near Bourton-on-the-Water, where Ryknild joins the Fosse. There are three listed Romano-British sites in the village, including one just below the Lynches Wood. It is said that the Romans grew their vines on the clearly defined terraces there. Not far from the hill is the Kiftsgate Stone, the stone pillar marking the Kiftsgate Hundred. It is an ancient monument. Here in Saxon times, the Court of the Hundred met and public announcements were proclaimed. The Stone can be seen on the boundary of Weston Park, almost 200 acres of ancient woodland, first sold from the Giffard Estate in 1610. It still remains in private hands. A boundary stone at the south end of the parish was erected in the 18th century and has been designated as a listed building.
