The Prospect of Whitby claims to date from 1520. Ye Olde Cheshire Cheese says 1667. The Cittie of Yorke will tell you a pub has stood on its site since 1430. Write them all down and you have a crawl that spans five centuries of continuous London drinking. Except almost none of it is continuous, and very little of it is what it claims to be.

The Great Fire of 1666 burned 13,200 buildings across 400 acres of the City. Over a thousand taverns existed in London before that fire. The ones inside the City walls — which includes most of Fleet Street, Holborn, and everything down to the river — were destroyed. Every pub in the Square Mile that claims a pre-1666 date is, at best, a pub on an old site. The building itself is post-fire. Ye Olde Cheshire Cheese was rebuilt in 1667. The Cittie of Yorke survived the fire but was rebuilt anyway in 1695, then again in 1924. Southwark, outside the City walls, had its own fire in 1676 that took out The George Inn. Even the Prospect of Whitby — far enough east to dodge both fires — burned down in the early 19th century and was rebuilt. The flagstone floor is probably original. The rest is not.

What makes this interesting rather than depressing is that every pub on this crawl has made a choice about how to present its age. The George Inn performs authenticity through its galleried courtyard, which is genuine 1677 construction — but the Great Northern Railway demolished two-thirds of the building in 1889 for warehouses, so you’re looking at one surviving wing of something that was once three times larger. The Cittie of Yorke performs it through a cavernous Gothic interior with thousand-gallon wine vats above the bar, which feels medieval but was designed by a wine merchant in 1831 and reconstructed in 1924. The Black Friar doesn’t perform age at all — it performs the idea of monastic history through an Arts and Crafts interior so extravagantly decorated that it was nearly demolished in the 1960s before John Betjeman stepped in.

The route runs from Fleet Street to Wapping, roughly east, crossing the river at Blackfriars Bridge and following the south bank before cutting down to the Thames at the end. You can walk it in a day. We’d suggest starting around noon — Ye Olde Cheshire Cheese and Ye Olde Mitre both close early on weekends, so check times before you go. The longest stretch is the walk from Southwark to Wapping along the river, which takes about 25 minutes and is one of the better riverside walks in London if the weather holds.

Dickens drank in at least four of these pubs. Samuel Johnson in at least two. Pepys in at least one. Turner painted from one. None of this makes the beer taste different, but it does make you pay attention to the rooms you’re sitting in — the vaulted ceilings, the flagstone floors, the gallery balconies — in a way you wouldn’t in a normal pub. Whether any of it is genuinely 500 years old matters less than the fact that someone, at some point, decided it should look like it was.