When the last glacial period ended, the hunter gatherers of the Palaeolithic period followed the animal herds across the land between continental Europe and Britain. Then, as conditions continued to improve and vegetation became more able to support a greater diversity of animals, the annual range of seasonal movement by Mesolithic communities decreased, and people became more fixed to particular localities. Until about 6,000 BC, Mesolithic people appear to have exploited their environment as they found it. As communities came to rely on a smaller territorial range and as population levels increased, attempts began to be made to modify or control the natural world. In the Great Wold Valley, pollen samples of Mesolithic date indicate that the forest cover in the area was being disturbed and altered by man, and that open grasslands were being created.
The Yorkshire Wolds became a major focus for human settlement during the Neolithic period as they had a wide range of natural resources. The oldest monuments found on the Wolds are the Neolithic long barrows and round barrows. Two earthen long barrows in the region are found at Fordon, on Willerby Wold, and at Kilham, both of which have radiocarbon dates of around 3700 BC.
From around 2000 to 800 BC, the people of the Bronze Age built the 1,400 Bronze Age round barrows that are known to exist on the Yorkshire Wolds. These are found both in isolation and grouped together to form cemeteries. Many of these sites can still be seen as prominent features in the present-day landscape. By the later Bronze Age, an open, cleared, landscape predominated on the Wolds. It was used for grazing and also for arable cultivation. The wetlands on either side of the Wolds in the River Hull valley, Holderness and the Vale of York were also being used for animal rearing at this time. In the Iron Age there were further cultural changes in the area. There emerged a distinctive local tradition known as the Arras Culture, named after a site at Arras, near Market Weighton. There are similarities between the chariot burials of the Arras Culture and groups of La Tene burials in northern Europe, where the burial of carts was also practised. The area became the kingdom of the tribe known as the Parisi.
After invading Britain in AD 43, the Romans crossed the Humber Estuary in AD 71 to invade the Northumbrian territory of the Parisi tribe. From their bridgehead at Petuaria they travelled northwards and built roads along the Wolds to Derventio, present day Malton, and then westwards to the River Ouse where they built the fort of Eboracum. There is evidence of extensive use of the light soils of the Wolds for grain farming in the Roman era. Several Roman villas which were the centres of large agricultural estates have been identified around Langton and Rudston. In the low-lying lands on either side of the Wolds there was an increase in the number of settlements between 500 BC and AD 500, as the land became drier and more accessible due to a fall in sea level. The lower-lying land was used for stock breeding. During the last years of Roman occupation Anglo-Saxon raiders were troubling the area and, by the second half of the 5th century, settlement by Anglian invaders was taking place in east Yorkshire. Village names containing the elements -ing, -ingham or -ham are Anglian settlement names. As Christianity became established in the area from the 7th century onwards, several cemeteries like the one at Garton on the Wolds show evidence of the abandonment of pagan burial practices. In AD 867, the Great Danish Army captured the Anglian town of York, and the remnants of the army settled in Yorkshire from AD 876, when their leader Halfdan shared out the land among them. Scandinavian settlements have names including the elements -by and -thorpe. Scandinavian rule in the area came to an end in AD 954 with the death of their ruler Eric Bloodaxe.
After the Norman Conquest of England by William the Conqueror in AD 1066, the land in the East Riding was granted to followers of the new Norman king and ecclesiastical institutions. When some of the northern earls rebelled, William retaliated with the Harrying of the North which laid waste to many East Riding villages. The land was then distributed among powerful barons, such as the Count of Aumale in Holderness and the Percy family in the Wolds and the Vale of York. These lay lords and ecclesiastical institutions, including the monasteries, continued to improve and drain their holdings throughout the Middle Ages to maximise the rents they could charge for them.
In the mid-16th century Henry VIII of England dissolved the monasteries, resulting in the large areas of land owned by Meaux Abbey, Bridlington Priory and other monastic holdings being confiscated. The Crown subsequently sold these large tracts of land into private ownership. Along with the land already belonging to lay owners, they formed some of the vast estate holdings which continued to exist in the Riding until the 20th century.
The 18th and 19th centuries saw first the expansion of canals and then the construction of rail links. The River Derwent was canalised as far upstream as Malton and was linked to Pocklington by the cutting of the Pocklington Canal. Other canals were cut to join the towns of Beverley and Driffield to the River Hull, which was also improved to aid navigation. The Market Weighton Canal connected the town directly to the Humber Estuary. An early rail link was constructed between Filey and Bridlington in 1847 and the Malton to Driffield railway was the first to cross the Wolds in 1853. These routes primarily served the agricultural community in helping to get their products to the expanding industrial markets in the West Riding of Yorkshire and to the port of Hull for export. The rail links served also to transport holidaymakers to the expanding coastal resorts of Bridlington, Hornsea and Withernsea. The canals and canalisation of some of the rivers helped to aid drainage in such of the low-lying ill-drained areas that then still existed. The landscape in the East Riding had changed little since the enclosure of the open fields in the 18th and 19th centuries, except for the removal of some hedgerows to allow for the use of large agricultural machinery in the 20th century.