High Street, together with Wine Street, Broad Street and Corn Street, is one of the four cross streets which met at the carfax, later the site of the Bristol High Cross, the heart of Bristol, England when it was a walled medieval town. From this crossroads High Street runs downhill south-east to Bristol Bridge, a distance of approximately 155m. . . . High Street, together with Corn Street, Broad Street and Wine Street, formed the earliest nucleus of Bristol. It is shown clearly on Ricart’s Plan, one of the first English town plans, with the High Cross at its top and St Nicholas Church (which then incorporated the town’s southern gate) at its foot. The street appears to have changed little by the time Millerd’s Citty of Bristoll map was published in 1673. . . . Puritan diarist Nehemiah Wallington describes Bristol Bridge and High Street in the 17th century as containing the chief shops of mercers, silkmen and linen drapers. Those who could not get premises on the bridge, which at that time was lined with shops, considered High Street the next best location.
By the mid-19th century shop fronts lined the slope of High Street, and development continued into the 20th century. Thomas Jones, the Pembrokeshire draper whose department store eventually became part of the Debenhams group, acquired three shops on High Street, ten on Wine Street and three on Mary le Port Street. In the 1920s the firm even tried to buy the landmark Dutch House which stood on the corner of High Street and Wine Street; when that bid failed the firm embarked on a modernisation programme which was almost complete by 1940. The majority of buildings on the east side of High Street were destroyed by aerial bombing on 24 November 1940. St Nicholas Church, also damaged by bombing, was subsequently repaired and brought back into use.