Square-Mile-ophile: Five oldest pubs in the Square Mile

The title of London’s oldest pub has been fought over for years and no area of the capital has quite as many contenders for the title as the Square Mile.

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Do pubs, like a fine wine, get better with age? We think in this case, yes they do…as long as you’re fond of creaking floorboards, low ceilings and the odd scruffy carpet.

Many of London’s original boozers were burnt to the ground during the Great Fire of 1666. This has meant that many of the city’s oldest pubs date back to around 1667.

Back in the 17th Century London’s pubs were as much a centre for the capital’s social life as they are now. But thankfully they are no longer thought of as dens of iniquity and used as places venues for cockfighting. Well, most of the time.

Here’s the oldest and the best that the City of London has to offer.

Map of the Square Mile's oldest pubs

Map of the Square Mile’s oldest pubs

1.  Olde Cheshire Cheese, 145 Fleet St, EC4

Now the name does give this place away slightly but they are one of the few pubs in London that can really justify it.

The pub was destroyed during the Great Fire of London and so the official date on the pub is 1667 however the pub’s vaulted cellars are thought to date back to a 13th century Carmelite Monastery. That pips the other pubs for us.

The entrance to the pub lists the reigns of 15 monarchs through which the pub has survived. Once inside, the pub is a series of warren like corridors and staircases that confuse the most regular of punters.

2. The Hoop and Grape, 47 Aldgate High Street  Greater London EC3N 1AL

This building is one of the few surviving timber framed pubs from before the Great Fire. According to local legend the flames halted just 50 yards from the building.

Built in 1593 and originally called The Castle, then the Angel & Crown, then Christopher Hills, finally becoming the Hoop & Grapes – referring to the sale of both beer and wine – in the 1920s.

This pub has a classic higgledy-piggledy frontage with slightly crooked Tudor panelling and sash windows that have survived since the 1720s. If you look closely you’ll notice that the front of the building leans out slightly but has been fortified following extensive restoration.

3. Jamaica Wine House, St Michael’s Alley, EC3

Jamaica Wine House, St Michael’s Alley, EC3

Jamaica Wine House, St Michael’s Alley, EC3

As one of the oldest parts of London, the Square Mile acts like a labyrinth of alley ways, many of which harbour some of the oldest drinking holes around. St Michael’s Alley is one of the prettier. And of course, a meander down the lane leads intrepid explorers to Jamaica Wine House.

The pub door sits very closely to a blue plaque which reads, ‘Here stood the first London Coffee house at the sign of the Pasqual Rosee’s Head 1652.’ The original coffee house was a favourite haunt of Samuel Pepys.

Known locally as the “Jampot” this little pub is definitely a top historical pit stop.

4.  Ye Olde Watling, 29 Watling St, EC4

Built in 1668 (yes another Great Fire phoenix) the pub is reputed to have been built from ships timbers by Sir Christopher Wren himself. Not only did the great architect build the pub but he apparently set up shop and used it as his drawing room during the building of St Paul’s Cathedral.

Oh and of course Wren’s army of builders used the pub during the post-fire rebuilding mission of 1667.

If you’re as fond of Guinness as you are of history – word has it Ye Olde Watling produces a mean glass of the “black stuff”.

5.  Old Bell, 95 Fleet St, EC4

We go back to Fleet Street for our last historical drinking hole. This pub was another of Wren’s creations – where did he find the time?

The pub is on the site of one of the first ever printing presses around 1500 and kept the resulting media industry lubricated until the newspapers’ sad exit from Fleet Street during the eighties.

Out the back, the pub opens out on to the courtyard of St Bride’s Church - one of Sir Christopher Wren’s most gorgeous constructions.


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Readers' comments (2)

  • Was going to suggest Ye Olde Mitre. But Time Out tells me: "The date on the sign says 1547, but this version of the Mitre was actually built around 1772"

    Wonderful place for a pint if you're ever out near Hatton Garden.

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  • Great item - the Old Doctor Butlers Head in Moorgate will not be far off that top 5 list. In March it will be hosting a whole group of new pub start up entrepreneurs - where People 1st will turn its licensed trade research into gold dust!

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