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The Herberts of Cherbury were the dominant landed and political power in Montgomery from the time of Henry VIII, albeit with occasional interference from other branches of the family. They took their name from Chirbury, a village in Shropshire, some three miles from Montgomery, and several of the family represented Montgomery in Parliament. Their chief residence lay near Montgomery, and was known variously as Blackhall, Lymore, Lysmore or Llys-mawr. The family also had a house at Llysyn.

The lordship of Chirbury was acquired in 1553 by Edward Herbert (d. 1593) of Montgomery from his second cousin, William Herbert (d. 1570), earl of Pembroke. Edward also acquired the Castle Island estate in the upper valley of the river Maine, east of Tralee in Ireland, after it was forfeited by the earl of Desmond. His elder sons, Richard (d. 1596) and Mathew, were the true founders of the Herbert families of Cherbury and Dolguog.

Among Richard Herbert's sons were Edward Herbert (d. 1648), the metaphysical poet George Herbert (d. 1633), and Sir Henry Herbert, Master of the Revels (d. 1673). The eldest son, Edward, inherited his father’s political and landed interests, while his brothers moved away and played little part in the affairs of Montgomery. Edward was succeeded by his son, Richard Herbert (d. 1655), a royalist commander, whose son, Edward (d. 1678), made amends with the Protectorate, but the family were never fully at ease until the Restoration in 1660. The family’s position was secured by Edward’s son, Captain Henry Herbert (d. 1691), who supported William of Orange in 1688, having previously joined his father in Booth's royalist rebellion in 1659, and fought in the French army in the Dutch war in the 1670s. He was succeeded by his son and grandson, both also called Henry (d. 1709 and d. 1738 respectively), the former of whom had already purchased the Worcestershire manor of Ribbesford.

The Dolguog Herberts resided at Plas Dolguog, near Machynlleth, and Oakley Park, near Llanidloes.