Pints & History: Islington to Duke of York Square Pub Walk
A tavern crawl through London's rich history, eccentric characters, and legendary boozers
London · 12 stops · 7.9 km · ~2.3 h · Generated
-
1. King's Head
115 Upper St, London N1 1QN, United Kingdom
Standing in front of number one hundred and fifteen Upper Street, you are looking at a venue that transformed London culture. A tavern has occupied this site since fifteen forty-three. But the most legendary chapter of the King's Head began in nineteen seventy, when an American theatrical producer named Dan Crawford walked into what was then a run-down local pub.
Crawford saw magic where others saw rubbish, transforming the dark back room—which had been used as a pool hall and a boxing ring—into London's very first pub theatre since the age of Shakespeare!
This intimate, slightly chaotic space became a launchpad for world-famous talent. Long before they were household names, performers like Alan Rickman, Joanna Lumley, and Victoria Wood treaded these boards. In fact, Hugh Grant made his professional acting debut right here, performing in front of audiences sitting so close they could almost touch the actors.
Yet Dan Crawford was equally famous for another, delightfully stubborn quirk: he flatly refused to accept Britain's new money!
When the United Kingdom decimalised its currency in nineteen seventy-one, replacing shillings and pence with modern coins, Crawford simply ignored the change. For over twenty years, the bar operated in old money. Bartenders rang up drinks on an antique early twentieth-century till, and customers buying a pint had to calculate their bill using pre-decimal conversion charts.
Step inside, take in the traditional bar and historic charm, and imagine the brilliant actors and eccentric visionaries who raised a glass right where you are standing.
-
2. The Camden Head
2 Camden Walk, London N1 8DY, United Kingdom
Tucked away in the narrow, cobbled alleyway of Camden Passage, surrounded by antique stalls and vintage shops, stands the Camden Head. While a pub has refreshed thirsty passersby on this site since the seventeen eighties, the striking pink-brick Victorian building you see today dates from eighteen ninety-nine, built right at the climax of London’s golden age of pub design.
Step inside, and you will notice how the pub preserves the glamorous feel of a late nineteenth-century gin palace. Notice the central circular island bar, the curved etched glass windows, and the ancient clock crafted by Pond’s of Clerkenwell. Look closely around the interior and you might even spot an original Victorian waiter bell mechanism mounted on the wall.
But what truly sets this Islington institution apart is what happens right upstairs.
Up in the first-floor function room, behind stained-glass windows saved from demolished London houses, lies one of the city's most legendary incubators of British comedy. Since the arrival of the Angel Comedy Club, this modest room has hosted free stand-up shows seven nights a week.
Stars like Stewart Lee, Joe Lycett, Nish Kumar, and Harry Hill have all taken the tiny stage here to test out brand new jokes on intimate audiences.
If you hear sudden roars of laughter echoing down to the street, you know a future superstar is probably testing their material above your head.
Outside, the terrace offers a perfect vantage point to sip a pint while watching market bargain hunters haggle over silver spoons and rare trinkets, bridging two classic Islington traditions in one remarkable spot.
-
3. Old Red Lion Pub & Playhouse
418 St John St, London EC1V 4NJ, United Kingdom
Look up at the ornate red-brick facade of four hundred and eighteen St John Street and notice the carved lettering near the top gable. It reads, "The Old Red Lion fourteen fifteen, Rebuilt eighteen ninety-nine." That date is no marketing gimmick. A tavern has stood on this exact spot for over six hundred years, making this one of the oldest continuous pub locations in London.
Back in fourteen fifteen, when King Henry the Fifth was fighting at Agincourt, Islington was not a dense urban neighborhood. It was a tranquil village of open fields and country lanes. St John Street was part of the Great North Road, the primary highway entering London from the north. Day and night, cattle drovers trudged down this dirt road, herding sheep and cows from northern pastures toward the great meat market at Smithfield! The original timber pub stood alongside cattle pens and a farm called Goose Farm, providing drovers with a warm hearth, a heavy meal, and a tankard of ale before they entered the City.
Because Islington lay outside the legal jurisdiction of the City of London, the Old Red Lion also became a refuge for political dissenters, writers, and artists. In the late eighteenth century, the radical thinker Thomas Paine sat in the pub’s garden writing parts of his revolutionary masterpiece, "Rights of Man." The painter William Hogarth frequented the bar and included the tavern in his seventeen thirty-eight artwork, "Evening." Over time, iconic figures like Dr. Samuel Johnson, Oliver Goldsmith, Karl Marx, and George Orwell all drank here.
The pub archives contain some astonishing tales. Records show a bitter twenty-seven-year legal feud starting in fifteen hundred between the landlord and licensee over sky-rocketing rent, showing that London rent disputes go back centuries! Another record from fifteen twenty-seven describes a fatal sword duel outside, after which the victim's body was stored in the attic for days while waiting for the magistrate to arrive.
The present Victorian building dates from eighteen ninety-nine, complete with red granite pillars and carved lions. But its identity shifted again in nineteen seventy-nine. The upstairs room, which had spent decades as a boxing ring, was converted into a sixty-seat black box theatre. Today, the Old Red Lion Pub and Playhouse is a celebrated fringe theatre venue, launching groundbreaking new plays while honoring over six centuries of London history.
-
4. The Wilmington
69 Rosebery Ave, London EC1R 4RL, United Kingdom
-
5. The Queens Head
64 Theobalds Rd, London WC1X 8SF, United Kingdom
-
6. Princess Louise
208 High Holborn, London WC1V 7EP, United Kingdom
-
7. Bloomsbury Tavern
236 Shaftesbury Ave, London WC2H 8EG, United Kingdom
-
8. The Crown & Two Chairmen
31-32 Dean St, London W1D 3SB, United Kingdom
-
9. The Red Lion, Mayfair
2 Duke of York St, London SW1Y 6JP, United Kingdom
-
10. The Bag O' Nails
6 Buckingham Palace Rd, London SW1W 0PP, United Kingdom
-
11. Plumbers Arms
14 Lower Belgrave St, London SW1W 0LN, United Kingdom
-
12. The Antelope
22 Eaton Terrace, London SW1W 8EZ, United Kingdom
