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Whitby is prettily situated at the mouth of the River Esk, on the Yorkshire coast, and is about midway between the Humber and Tyne. Built on the two banks of the river, it has a quaintness which is due to the inhabitants in previous centuries erecting houses as near the water as possible, which is easy to understand, considering that the town owed the importance it possessed to its connection with the sea. There are traces of the existence of the town in the days of the ancient Britons, and though at the present day the traces of the ancient inhabitants have disappeared, the place-names of particular localities in the vicinity remain as evidence.
Earth work remains exist which are known as the Killing Pits an area full of circular cavities near Goathland and in other parts of the district, and other remains go to prove that the place existed in the time of the Druids. Such places are the ruins of ancient villages and the tumuli on the moors which have yielded remains of the dead inhabitants of pre-Roman times. Flints have also been found in the near neighbourhood of the town which tell their own tale of the lives of those who inhabited the district at this period. Of the Roman occupation there are abundant proofs, including camps at various places, and from York a Roman road can be traced to Dunsley Bay, although there is no testimony on record that a Roman station existed there. Bede, who wrote two hundred years after the departure of the Romans, interprets Streonshalh, the name of the bay at the time, as Sinus Fari "the Bay of the Lighthouse. Roman antiquities have never been known to be found on the site of Whitby, but have been discovered within a few miles.
Coming to Saxon times, the name Thordisa proves there was a temple to Thor, the god of Thunder, at Eastrow, two miles west of Whitby, and the history of the place is much more easily traced from the time when Penda, King of Mercia, was slain in a battle with Oswy, King of Deira. Thenceforward, the history of the town is revealed in the story of the successive Abbeys which have stood on the East Cliff.
The monastery and the town of Streonshalh were destroyed by the Danes in 867, and both lay desolate for two hundred years.
The Danes were the next invaders to attack the Britons, and the Kingdoms of East Anglia and North Umbria, embracing the whole coast of Yorkshire, were totally destroyed by their inroads. This part of Yorkshire became the special habitation of these invaders, where more of their language survives in provincial words and place-names than in any other neighbourhood.
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A change came with the Norman conquest, and in William’s distribution of territory to his followers, Whitby and its dependencies and the manors of Hinderwell and Lofthouse were conferred on the Conqueror’s nephew, Hugh de Abrincis, Earl of Chester, under whom William de Percy held Whitby Abbey and the lands belonging to it. The Percys were the chief benefactors on the re-establishment of the monastery, which took place in 1074. Whitby, like its predecessor Streonshalh, rose as a ependency of the Abbey. The name has been said to mean White village, from the aspect of the new erections; and the place was also known as Priestby or Priest village, about the time of the Conquest.
The Domesday survey provided us with the place-names of the district in 1080, and the domains included Whitby, Stakesby and Newholm, with the manor of Lofthouse, and the lands at Hinderwell, Boulby, Easington, Guisborough and elsewhere. Indeed, most places in the district surrounding Whitby are mentioned in Domesday, and there are few places there mentioned which have been lost with the lapse of time; so that by far the greater part of the names of villages and hamlets in the locality
As the Abbey grew in riches, the town increased in size and importance, and began to extend itself along the east bank of the Esk, where Church Street now exists; and as the " port " of Whitby was granted to the monks by William de Percy, and the " fishermen " of Whitby are noticed about the same period, it follows that the lower part of the town must have been inhabited soon after the Conquest, if not before. In process of time, the largest portion of the town was situate below the cliff, most of the secular inhabitants having their houses on the banks of the river, the upper portion being chiefly occupied by the offices of their liberality; Peter, the succeeding Abbot, obtaining the monastery, and dwellings of its immediate servants and dependants.
Before the year 1189, Whitby had become so considerable that Abbot Richard de Waterville granted his Charter for creating it into a free borough, with privileges similar to those granted to other boroughs of the period. The liberties of the inhabitants, however, were of short duration, for the monks were jealous of their rights, and repented of from King John a repeal of the Charter. William Clerk, Ralph the son of Ludof, and Simon de Keseburn are recorded to have vainly resisted this withdrawal of the town’s rights.
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The principal streets of Whitby are of ancient date. Flowergate is named in a charter granted in the time of Roger, who was abbot from 1222 to 1224; and among the witnesses are William the merchant and William the dyer. Hacklesougate (Haggersgate) is named in 1296, Kirkgate or Church Street in 1318; and about this period there appear the signatures of Alexander the weaver; William the fuller; and William the Smith. Grape Lane is known to have had houses on both sides in 1595, and Bridge Street and Sandgate, especially the former, are fully as old, if not older than Grape Lane. Baxtergate is mentioned in 1574, and the title deeds of a house near the bridge disclose the name John Carlill, whose occupation in 1598 was that of a jet worker. Bagdale is not named in 1595; and Bagdale Hall and a few houses close by are spoken of a being "nere unto Whitbie." In the last-named year there were houses adjoining Skate Lane (now Brunswick Street).
The streets of the period were little more than unpaved roads, with thatched cottages at the sides, standing apart in pieces of land or garden ground.