The origin of the name of this ancient street is undoubtedly bound up with the origin of the name Bradford. Morant the Essex historian (1768) suggests that Bradfords Farm (Little Bradfords) takes its name from the family of Bradford who lived there in the reign of King John (1199-1216). Mr. Alfred Hills, a local historian who lived at No. 11, The Old House, wrote that the origin of the name of this ancient street was a corruption of Broad Ford over the River Pant; the origin of the name Bradford is from the Saxon for a broad ford.
The street follows the old Roman road that ran from Chelmsford to Long Melford, built to allow the rapid movement of troops to quell any unruly Celts. In the great age of Pilgrimage, it was on the pilgrim route between Canterbury and London to Bury St. Edmunds and Walsingham. Special inns were built in Braintree to accommodate the pilgrims and there was a Pilgrims' Hostel, St Jame’s, believed to be near the former Six Bells.
The origins of the Bradford Street mill date back to 1303. About the year 1520, Bocking was a center of extensive trade in woollen cloth. Most early houses were made of timber and wattle and daub construction, since there was no suitable building stone within easy reach and roads were bad or impassable for heavy materials. There was still plenty of good oak, as some forest land remained uncleared. The height of the wool trade in Bocking was the early 18th century when the name of Bocking described a distinct type of cloth, and large fortunes were made by famous Essex families. The Ruggles of Bradford House bought an estate in Finchingfield. The Nottages, five generations of whom lived at Fulling Mill House (Convent), became bankers. Robert Maysent made "The first Long Bay" whilst another branch of the Maysent family lived at Maysent House.
Bradford Street also had a number of Wool Halls, where weekly sales of yarn and cloth took place. It is interesting to note the frequency with which the names of wool traders were linked with the management of pubs, and the great number of inns which from time to time existed in the street. In 1725 Cox wrote "Bocking is famous for its Bay Trade and many rich clothiers live there in fine spacious houses"