A Boozy Walking Tour of London’s Oldest Road —

Two thousand years ago, Roman navigators followed a great river to a series of islands, where the passage narrowed enough to install a timber bridge 100 metres from where a barista at the London Grind has just denied me almond milk for my latte. Instead, he slides a far more fashionable oat–milk latte along the marble bar. When in Roman London, as they say.

The coffee fuels me for a nine–kilometre walk along London’s first road, paved by the Romans in the first century. Marked on maps with the transit route name A10, the strip switches identity every few blocks as it stretches north from London Bridge through the City financial district, Shoreditch, Dalston and Stoke Newington, all the way up to Seven Sisters Road. Slicing east from west and connecting Vietnamese, Caribbean, Turkish and Jewish communities, the road is a cross–section of the city.

I’ve spent enough time stalking these sidewalks to hollow out grooves like those from a Roman chariot. My house backs onto the A10, after all. But when I moved here 10 years ago, I couldn’t convince visitors to think of it as anything but a conduit to Soho or Notting Hill. That was then. I’ve since witnessed a slow, steady change: start–ups, pop–ups, art fairs, craft stout replacing Stella Artois. Visitors have started to come around, quite literally.

“The bridge made the road,” says historian and archeologist Kevin Flude, meeting me at the spot where the earliest London Bridge segued into a thoroughfare called Fish Street Hill. Archeologists found evidence here of Roman colonnades built two millennia ago during the early settlement of Londinium. Back then, the road doubled as a barometer for the city’s cultural heat. Beneath today’s skyscrapers sat first–century warehouses for olive oil and wine. Below the glass arcades of Leadenhall Market – a current destination for imported cheese and shoeshines – was a sprawling marketplace. And behind the Victorian pillars and coffered ceilings of the Crosse Keys pub stood a forum comparable to Rome’s. So: very hot.

Flude pulls me around a corner to point out remnants of the original city walls at All Hallows Church. I, meanwhile, point out a half–dozen towers built since the turn of the millennium, when London’s financial boom tore back the red tape for supertall construction. Each has a power restaurant – Sushisamba, City Social – drawing evening revellers downtown for the first time in decades.

I leave the old walls for the brick ateliers of buzzy Shoreditch and turn into a gallery/disco/café/creative collective called Dream Bags/Jaguar Shoes. The sun streams in as I pull up a stool at a bar spray–painted with a scrawl of acid colours. Co–owner Teresa Skrgatic, a freckled brunette in a black denim jumpsuit and high–tops, pours me a half–pint of unfiltered And Union lager. Straining to be heard above an afternoon playlist of post–punk and guilty–pleasure disco, she reminisces about the early 2000s, when she and her brother were among the first artists to set up here. They hauled in picnic tables, threw up their friends’ street art and named their gallery after the previous tenants, importers–exporters of bags and shoes.

With the windows flung open, passersby in threadbare T–shirts lean in, prompting waves from Skrgratic. Some pile in around tables with pints; an artist flips through phone pics for Skrgratic to consider for an upcoming exhibition. Except for the signatures on the floor–to–ceiling wall paintings, little has changed in 16 years. It hasn’t had to. Copycats like the Ace Hotel, which has brought in burly bouncers to filter through the creatives relocating from Soho, have only sparked more interest in the original.

Ten minutes north, the road arcs over the Regent’s Canal, humming now with hand–painted narrowboats and waterside cafés after years of neglect. I’m in Dalston, erstwhile habitat of gangsters and Quakers. Slim, single–bay houses built for artisans in the 18th century now sell vintage Martin Margiela overcoats (two sizes too small, alas) and Korean fried chicken (devoured guiltlessly because it’s billed as “artisanal”).

Only devoted drinkers can keep up with Dalston’s slew of bar openings. I settle in the speakeasy Three Sheets and warm up with an Every Cloud, a reckless combination of tequila and lager. Should I be mixing tequila and beer? Do I care? I do not. Another few steps, another few bars and I teeter into Untitled, which combines the local passion for concrete and communal seating with the apparent craze for cocktails served in minuscule goblets. I sip the Violin, a snifter packed with oak, pine, beeswax, benzoin and black–pepper vodka, and before long, I catch myself communicating with the black and white S&M photos on the wall. It’s time to turn in.

Too early the following morning, I’ve advanced four blocks up from Dalston to meet Sean Gubbins, a tour guide with Walk Hackney, who has kindly offered to guide me on my next leg. We’re momentarily caught in the scrum of Ridley Road Market, a hodgepodge of outdoor produce stands that catered to genteel Victorians, then Jewish immigrants and now Afro–Caribbeans and Turks. “The only real difference is now they sell mangoes,” Gubbins tells me.

Thought to be the former grounds of King Henry VIII’s hunting lodge, the village–y section of Hackney north of the market was a backwoods until the restoration of the monarchy and Anglican church sent Nonconformists and religious outcasts up here to settle. Same vibe, different age. Arty types, priced out of Shoreditch, have migrated nearby, like Skrgatic’s former bartender, who opened his own place, a tiki spot called Ridley Road Market Bar. But when they have babies, they find more suitable houses a kilometre farther in Stoke Newington.

“The last boom here, 150 years ago, tripled the population,” says Gubbins. That was thanks to steam trams and then motor trolleys, which replaced horse–drawn buses and coaches. Today, the new Overground train line has activated another wave of openings. “It’s less a growth spurt than a tsunami,” he says, stepping out of the path of double strollers.

We pass retirees hunched over chessboards and pierce a cloud of vape smoke outside Z Bar to pick up triple–shot cappuccinos and freshly squeezed orange juice. The smell of Turkish flatbread leads to nearby kebab shops, where women knead dough in the window. And then Gubbins glimpses someone buffing a patch of bright blue tilework up the road. It’s the grand opening of Fanny’s, a crowd–funded “concept” kebab shop that advertised itself as a “posh” alternative to the area’s signature snack, until local outcry prompted them to drop “posh” from their signage. (The twee and the traditional, it turns out, don’t always get along.)

In the shade of mature plane trees, we pass women in head–scarves and Hasidic men in massive fur shtreimels, and hop the train to Seven Sisters Market, a ramshackle Latin American marketplace. Hair dryers whirr from coiffure stalls, competing with piped–in samba and the laughter of children eating fresh pineapple. At Pueblito Paisa café, we grab seats on the patio next to families watching soccer on big screens. The server delivers thick cinnamon hot chocolate and dessert–cheese buns he calls “sweetmeat bread.” I experience that frontier feeling one might have felt years ago in Stoke Newington or Dalston or all those neighbourhoods behind me, when new arrivals to London were making their mark.

Starting the gentle descent south, we approach Stamford Hill. Gubbins stops me and gestures down through the trees toward minarets, steeples and towers. “After Queen Elizabeth I died in 1603, James VI of Scotland took this road to meet the leaders of the city before his coronation,” he says. “As they welcomed him to the new capital, this was his first glimpse of London.” I wonder what he’d think if he could see it now.

Roamin’ Road

Plan your walk from London Bridge to Pueblito Paisa café.