In 998 the cathedral became a Benedictine monastery and the Bishop’s seat later moved to Old Sarum. Following the Dissolution under Henry VIII in 1539, Sherborne Abbey and the vacated monastic buildings were acquired through the covert manoeuvres of Sir John Horsey of Clifton Maybank and sold to the townspeople. The majority of the buildings are now occupied by Sherborne School, while the former east gatehouse and almonry are today home to Sherborne Museum.

In the 12th century Roger of Caen, Bishop of Salisbury and Chancellor of England, built a fortified palace at Sherborne. It became the home of Sir Walter Raleigh, who in 1594 constructed a mansion on the site of a former hunting lodge in its grounds. Today this is known as Sherborne Castle. During the English Civil War, the old palace was destroyed by General Sir Thomas Fairfax and the Parliamentarian Forces. Its ruins are now in the care of English Heritage. 

Sherborne rose to prominence in the medieval period as a centre of cloth making and a number of its most picturesque buildings date from this time. St. Johns’ Almshouse, the best surviving example of a medieval almshouse in Wessex, and the Church House on Half Moon Street, both bear witness to the wealthy patronage of the town’s mercers and clothiers. In 1540 the antiquarian, John Leland, described Sherborne as “the best town at this present tyme in Dorsetshire.”

Sherborne’s markets and fairs drew in farmers and artisans from the wider agricultural district. The burgeoning industries of gloving and silk throwing, meanwhile, relied heavily on outworkers from the surrounding villages. The town’s favourable position on two main coaching routes (linking the area with London, Exeter, Bristol and Weymouth) encouraged further expansion and, from the 1860s, this was accelerated by the arrival of the railway. By the outbreak of the First World War, Sherborne boasted a large silk mill, two glove factories, two breweries, two dairies, a gasworks and a steam laundry.

Although major industry has since declined, Sherborne is famous for its schools and education and prides itself on its independent shops, galleries and artisan crafts. The town’s architectural beauty and aura of spirituality has made it attractive to artists and writers, including Sir Thomas Wyat, Charles Dickens and the Powys family. Sherborne features in the writings of Thomas Hardy as “Sherton Abbas.” His novel The Woodlanders focused on its wider historic landscape with its orchards, coppicing and cider-making.  As well as providing inspiration for authors, Sherborne has been used for numerous film location settings including Goodbye Mr. Chips (1969), The Imitation Game (2014), Far from the Madding Crowd (2015), and Wolf Hall (2015).