One of the most ancient surviving forests in England, the Forest of Dean is a roughly triangular area bounded by the River Wye to the west and north, the River Severn to the south and the City of Gloucester to the east. Steeped in history, the forest goes back thousands of years and is the site of many Iron Age forts. Later it was used exclusively as a Royal hunting grounds by the Tudor kings, during which time it also became a major of source of iron. Timber from the forest was particularly fine and was regarded as the best source for building ships including Admiral Lord Nelson's ship, the Victory.

Sudeley Castle was built in the early 1440s by Ralph Botelier, a Member of the King's household and has royal connections spanning many hundreds of years, being in the ownership of the Crown for much of that time. The chapel, St Mary's Sudeley, is the burial place of Catherine Parr, the sixth wife of Henry VIII and contains her marble tomb. During WW2, the grounds accommodated a camp for Italian and German prisoners of war and the Castle itself became a 'safe house', where much of the Tate Gallery's picture collection was kept in safety from the blitz in London.

Berkeley Castle was constructed from 1117 A.D., on the orders of Henry II, with the aim of defending the Severn estuary and the Welsh border. It continues to belong to the Berkeley family, descendants of Robert Fitzharding, who completed the keep in 1153. King Edward II of England was held in the castle for 18 months, before supposedly being murdered there by unknown means, in 1327. The cell where he is supposed to have been imprisoned can still be seen. The castle has remained within the same family since its construction, with many areas now open to the public. It is the oldest continuously-occupied castle in England.

Two miles northeast of the Cotswold town of Winchcombe lies Hailes Abbey, a ruined Cistercian monastery. Founded in 1246 by Richard, Earl of Cornwall, the younger brother of King Henry III, the abbey became a major site of pilgrimage in 1270 when Richard's son donated a phial of the Holy Blood he had purchased from the Count of Flanders three years earlier. Dissolved in 1539, the abbey had, by the end of the 18th century, suffered extensive destruction but the ruins, now managed by English Heritage, still attract numerous visitors.