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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. However, 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). In the great age of Pilgrimage, it was on the pilgrim route, following the remains of the old Roman road from Canterbury and London to Bury St. Edmunds. Special inns were built in Braintree to accommodate the pilgrims and there is supposed to have been a Pilgrims' Hostel near the Six Bells.

From very early times the street was identified with the woollen cloth trade, 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. Maysent who lived at the Manor of Friars (Old Court) made "The first Long Bay" and built 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".

About the year 1520, Bocking was a centre 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.

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Date House Numbers Notable historical events  
1220 67, 69, 71 1215 Signing of Magna Carta.
1225-1250 75 1216-1272 Reign of King Henry III.
1380 7,9 1338-1438 Middle of the 100 years war.
1350 87 1348 1st Black Death.
1400 39,40 1399 Henry IV Crowned King of England.
1430 102,104 1429 Joan of Arc Unites France.
1450 84, 90, 68, 2, 89 1475 Thomas Wolsely born.
1475 13, 19, 21, 33 1492 Columbus discovers America.
1500 36,16,18,20 1509-1547 Henry VIII King of England.
1500 54,56,85 1534 Start of Protestant Church.
1520 114, 41  
1550 10,12,14,94  
1580 31, 106, 108 Mill  
1590 77, 79, 81 1588 Spanish Armada.
1550-1600 11 1558-1603 Elizabeth I reigned.
1600-1700 27,37,29 1599-1648 Oliver Cromwell.