A valley between Leebotwood and Caer Caradoc was important as a thoroughfare dating right back to Roman times. The eastern boundary of the village was formed from the ancient route of Watling Street which is still visible today. Caer Caradoc to the south of Leebotwood rises to a height of 1506 ft and is said to be one of the last strongholds of the native chief Caradoc or Caractacus who held out against the Romans.