The Saxons called it Giseldone in 1005 — Gīsla's hill — and the name took nearly a thousand years to become Islington. Through the medieval period, the Great North Road from Aldersgate passed through here, with a toll gate at The Angel marking the village limit. Liverpool Road, then known as the Back Road, served as a drovers' route where cattle rested before the final journey to Smithfield market; pens and sheds lined the road for the animals' accommodation. In the 17th and 18th centuries, Islington was a popular day-trip destination from London — close enough to reach by foot, far enough to feel rural. By 1716, Upper Street alone had 56 ale-house keepers, alongside tea gardens, archery grounds, and bowling alleys. The King's Head Tavern, which has occupied the same site opposite the parish church since 1543, offered music and dancing as the area's pleasures grew more sophisticated.

The Victorian railway era transformed Islington's social character entirely. As railway construction displaced the poor from inner London, many resettled in Islington — houses meant for single families were subdivided for many. The better-off left for the suburbs that the railways now made accessible. By the mid-20th century, Islington was largely run-down, a byword for urban poverty. Then came the Victoria line, the redevelopment of Angel tube station, and a wave of renovation that transformed the area's early Victorian and Georgian townhouses into desirable addresses. The irony is thick: the same poverty that had driven out the middle class for a century left a stock of intact Georgian buildings that became, once refurbished, exactly what the middle class wanted. The Blair-Brown 'Granita Pact' — the alleged political deal struck over dinner at a now-defunct Upper Street restaurant — became a shorthand for the political class that Islington, by then, had come to represent.

Few districts in England have been claimed by so many writers. Charles Dickens set scenes in Islington across at least six novels, from Oliver Twist to Our Mutual Friend. Anthony Trollope's The Way We Live Now lodged characters here. Neil Gaiman's Neverwhere named its fallen angel 'Islington,' after the Angel tube station. J.K. Rowling placed the Order of the Phoenix headquarters at 12 Grimmauld Place, a fictional street in the borough. Nick Hornby set About a Boy here. Martha Grimes's fictional detective Richard Jury lives in Islington. Douglas Adams wrote the place into his probability equations. The pattern suggests something real: Islington has always been a place of transit, of people moving through or settling unexpectedly, of lives interrupted and resumed. It is the kind of place that accumulates stories because it has always been just adjacent to the action — close enough to London's centre to matter, far enough from it to develop its own texture.

Angel tube station, which anchors the southern end of Islington High Street, has the longest escalator on the London Underground system at 318 steps. In 2007, a Norwegian man made international headlines by skiing down it. The station gave its name to the wider area — the Angel, Islington — after the famous Angel Inn that stood at the foot of Islington High Street from at least 1590. Nine inns lined the High Street at that time, along with a public pond. Islington is, according to the 2011 census, the most densely populated borough in the United Kingdom, with 138.7 people per hectare — more than twice the London average of 52. Arsenal football club's Emirates Stadium, with its sixty-thousand-capacity, sits at the northern end in Holloway. The Regent's Canal passes through the borough in an 886-metre tunnel, and bargees once walked their barges through it, braced against the roof in the dark.