Prehistoric remains abound in the district. Mesolithic flints have been found at Earlehillhead and other prehistoric stone tools come from Haugh Head and Langleeford. Where these early people lived is unknown but they probably travelled around the region on a seasonal basis to hunting grounds and other sources of food. Transhumance may well have been carried out, using the high summer grazing lands in the hills and retreating to lower altitudes such as the Milfield Basin in the winter. A possible long cairn has been discovered in the Harthope Valley on Scald Hill.
The earliest settlements in the parish date to the Bronze Age and lie high up the sides of the Harthope Valley at Long Crags, Tathey Crags and Snear Hill as well as at Hart Heugh. These unenclosed groups of hut circles survive in remarkable condition as upstanding earthworks and some have traces of field systems with clearance cairns. A more favourable climate in the Bronze Age allowed people to live and farm at such high altitudes. Evidence for the ritual side of Bronze Age life comes in the shape of burial cairns such as on Hart Heugh and a burial urn from Old Earle.
In the Iron Age and Roman periods the pattern of settlements began to change and a distinctive `Cheviot-type' settlement emerges. They do not have the roughly rectangular shapes seen elsewhere in the county and are built lower down the hillside than the earlier settlements. A large enclosed settlement can be seen at Long Crags and Carey Burn Bridge and traces of cord rig field systems lie nearby at Hart Heugh.
In medieval times people lived in small villages and hamlets at Middleton Hall and Earle. There were also other smaller settlements called shielings as found by the Harthope Burn and Carey Burn Bridge. Shepherds lived in shielings in the summer months whilst looking after sheep on high pastures.
The border family feuds of the so-called reivers in the late 16th and early 17th centuries meant that those who could afford to built defended farmhouses called bastles to protect themselves and their property from raids. A bastle in Earle was owned by two gentlemen who perhaps pooled their finances to be able to afford such a building. The valley of the Harthope Burn was the boundary of the English East and Middle Marches at this time.
As more peaceful times came to the area in the 18th and 19th centuries people began to invest more in their surroundings, building fine houses such as Middleton Hall. Agricultural improvements at this time saw a new farmhouse and farm buildings built at Langleeford, deep in the Harthope Burn valley. The access provided along the valley into the core of the Cheviots has meant many visitors to the parish. These include author Daniel Defoe and the novelist, poet and antiquarian Sir Walter Scott in the 18th century. Water supplies from the upland part of the parish were used to power water mills further down the valley, such as Earle Mill.
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