The town was once held to have been a Roman settlement, but no evidence shows this to be the case. Similarly, it is often linked to the monastery established by the Saxon monk Botolph at “Icanhoe” on the Witham in AD 654 and destroyed by the Vikings in 870, but this is now doubted by modern historians. The early medieval geography of The Fens was much more fluid than it is today, and at that time, the Witham did not flow near the site of Boston. Botolph’s establishment is most likely to have been in Suffolk. However, he was a popular missionary and saint to whom many churches between Yorkshire and Sussex are dedicated.

The 1086 Domesday Book does not mention Boston by name, but nearby settlements of the tenant-in-chief Count Alan Rufus of Brittany are covered. Its present territory was probably then part of the grant of Skirbeck, part of the very wealthy manor of Drayton, which before 1066 had been owned by Ralph the StallerEdward the Confessor‘s Earl of East Anglia. Skirbeck had two churches and one is likely to have been that dedicated to St Botolph, in what was consequently Botolph’s town. Skirbeck (map) is now considered part of Boston, but the name remains, as a church parish and an electoral ward.

The order of importance was the other way round, when the Boston quarter of Skirbeck developed at the head of the Haven, which lies under the present Market Place. At that stage, The Haven was the tidal part of the stream, now represented by the Stone Bridge Drain (map), which carried the water from the East and West Fens. The line of the road through Wide Bargate, to A52 and A16, is likely to have developed on its marine silt levees.[citation needed] It led, as it does now, to the relatively high ground at Sibsey (map), and thence to Lindsey.

The reason for the original development of the town, away from the centre of Skirbeck, was that Boston lay on the point where navigable tidal water was alongside the land route, which used the Devensian terminal moraine ridge at Sibsey, between the upland of East Lindsey and the three routes to the south of Boston:

  • The coastal route, on the marine silts, crossed the mouth of Bicker Haven towards Spalding.
  • The Sleaford route, into Kesteven, passed via Swineshead, thence following the old course of the River Slea, on its marine silt levee.
  • The Salters’ Way route into Kesteven, left Holland from Donington. This route was much more thoroughly developed, in the later Medieval period, by Bridge End Priory.

The River Witham seems to have joined The Haven after the flood of September 1014, having abandoned the port of Drayton, on what subsequently became known as Bicker Haven.[citation needed] The predecessor of Ralph the Staller owned most of both Skirbeck and Drayton, so it was a relatively simple task to transfer his business from Drayton, but Domesday Book in 1086 still records his source of income in Boston under the heading of Drayton, so Boston’s name is not mentioned. The Town Bridge still maintains the preflood route, along the old Haven bank.