The inhabitants of Peebles and Selkirk are a mixture of many races, the process of whose consolidation did not terminate till a Scottish king sat upon the English throne. Hence one may assert that over the Southern Uplands the tide of war has ebbed and flowed for more than two thousand years.

It was David I who began to civilize the Borders. By the time of the Alexanders, Scotland, and particularly the Lowlands, had attained a high degree of civilization. The Wars of Succession, however, checked this for many years; and no part of the Lowlands suffered more than Peebles and Selkirk. The connexion of the shires with these wars is not unimportant. The men of the Forest fought under Wallace at Falkirk; and the noble and handsome forms of those who fell roused the pitying admiration of the English Chronicler of the fight. Wallace after his desertion by the nobles at Irvine took refuge in the Forest; and a Peeblesshire baron, Sir Simon Fraser the younger, the patriot’s friend and companion-in-arms, and the hero of Roslin and of Methven, shared eventually Wallace’s fate. The Good Sir James was lord of Ettrick Forest. The Knight of Liddesdale, slain by his kinsman near Broadmeadows, was one of the band of heroes who won back from the English the castles they had captured in the time of David II.

In the fourteenth century the Borders on both sides were divided into three Marches: East, West, and Middle. Peebles and Selkirk were included in the Middle March. Over each March was set a Warden, and at stated intervals on days of truce Warden Courts were held. Thus grew up the Border Laws which dealt with fugitive serfs, and with offences committed by Borderers on either side of the boundary, such as manslaughter, and theft of goods or cattle. The first code of Border Laws was drawn up in 1249; the second exactly two hundred years after. They were revised from time to time till the Union, when they became null and void.

Various attempts were made to establish order; notably by James II in his contest with the Black Douglas, whose territory in Ettrick Forest he more than once invaded and whom he finally crushed at Arkinholm in 1454. James IV also made at least one famous expedition to the Forest, when he exacted submission from the "Outlaw Murray." Flodden, which so greatly enriched the fame and traditions of the Forest, gave only a short respite to the state of anarchy to which the Burgh Flodden Memorial, Selkirk Records of Peebles bear frequent and eloquent testimony. Brawls and fights in the streets, rapine, raid, and murder were the order of the day. The Tweedies of Drummelzier, the Scotts of Thirlestane, and other clans were neither "to haud nor to bind."

It was not, however, till the relentless persecution of Dacre after Flodden that life on the Borders was brought to a state of positive demoralization. "The Borderers," says Creighton, "ceased to regard themselves as bound by any laws save that of the family tie, and degenerated into gangs of brigands whose hand was against every man, and who made little distinction between friend and foe." Hence it is that James V is best known for his determined attempts to restore law and order upon the Borders. In 1529 he visited Peebles and Jedburgh for this purpose. The following year he resumed the task, and with a sufficient force followed the "Thief’s Road" across the Tweed, up by the Lour, round the Scrape and Dollar Law, then down the Craigierig Burn to Henderland, where he arrested William Cockburn. From there he went to Tushielaw, where he surprised Adam Scott, "the King of the Borders." The two blackmailers were taken to Edinburgh and executed. The Border Widow’s Lament commemorates the burial of Cockburn. But even these stern measures failed to awe the greater barons, whom James suspected of connivance at the depredations of their "kindly tenants." He, therefore, in the same year, caused several of them to be imprisoned. This alienated the Border barons; and James felt the bitter result of their defection at the rout of Solway Moss.

In the reign of Mary the war with England united the Borderers against their "Auld Enemy," and even Angus returned from exile to break a spear in defence of his country and the honour of his ancestors, whose tombs Latoun had defaced. The victory of Ancrum Moor roused Henry to fury, and the following year he dispatched Hertford to take vengeance on the Scots. The tale of his burnings and slaughterings is appalling. Peebles was burned to the ground with 250 towns and villages in the Tweed area besides towers and castles and monasteries. Three years after Henry’s death came peace between England and Scotland; and the lawlessness of the Borders grew more rampant than ever. On Queen Mary’s return from France, Moray was entrusted with the duty of restoring order. His policy—afterwards adopted by Morton and by James VI—was extermination. Yet one of the last Border raids—perhaps the most daring of all— was conducted in James’s reign by the king’s own Warden in 1596, when the "Bold Buccleuch" rescued "Kinmont Willie" from the castle of Carlisle. This deed, the fame of which resounded through Europe, nearly brought the two countries to war. It was about this time that the Border counties began to be known as the Middle Shires and a commission was appointed to establish order therein. Special courts were appointed in place of the old Warden Courts, at such places as Peebles, Hawick, and Jedburgh. Through the expeditious severity displayed by Dunbar the Commissioner at Jedburgh, "Jethart Justice" came to signify "hang first and try afterwards."

The Reformation had had little immediate effect upon the Borderers, nor did the constitutional and religious struggle of the seventeenth century strongly appeal to them. The enthusiasm for the Covenant was less ardent than in Galloway or Ayrshire, if an exception may be made for the west of Selkirkshire and for the Galashiels district. Yet when Montrose, seeking for support to the king, reached Kelso, he received little encouragement. Montrose advanced to Selkirk and took up his position at Philiphaugh. Leslie, receiving word of his proximity, marched with his main body on Selkirk, sending a force round Linglie hill to attack Montrose in the flank and the rear. At Leslie’s unexpected attack, the royal troops fled in rout over the hills to the west and north. Douglas and Montrose, cutting their way through Leslie’s lines, fled over Minehmoor, and reached Traquair House, where they were denied admittance. Making their way through the Tweed at Howford, they reached Peebles. From there, they escaped across to Clydesdale. In the year after his victory at Dunbar, Cromwell dispatched a force under Lambert to besiege Neidpath, held by the Earl of Tweeddale. The attack was made from the south side of the river and after a brave defence the Earl surrendered.

To the fiasco of the "Fifteen" Selkirk gave a supply of shoes and a contribution of £10. In 1745 the town of Selkirk, at the request of the city of Edinburgh, furnished the Pretender with 2000 pairs of shoes for his army. After Prestonpans, the Prince advanced towards England in two main divisions. The first column marched by Auchendinny to Peebles, thence to Broughton, Tweedsmuir, and Moffat. At Peebles the contingent occupied the field west of Hay Lodge, and the town-mills were kept busy on the Sunday to supply the troops with meal. The main column, under the command of the Prince, went by Lauder and Kelso, whilst the baggage party went by Galashiels and Selkirk. Charles Edward is said to have visited Traquair; but the Earl declined to join his cause, and to soften his refusal, declared that the gates would remain closed till Charles Stewart re—entered them as Sovereign of the Kingdom.