A Walk Through London’s History

London Bridge Loop

6 miles / 9.7km
See walk variations


Tower of London l Tower Bridge l The Monument l Charterhouse l Dick Whittingdon’s House l St Dunstan in the East l St Paul’s Cathedral l Guildhall l Old Bailey


Discover the out-of-the-way pieces of history scattered around London’s square mile on this great walk, perfect for a lazy Sunday. The route starts at London Bridge and loops across the Thames to take in the Tower of London before diving into the narrow cobbled lanes behind familiar thoroughfares like Cannon Street where you’ll discover historic priories, church ruins and the oldest house in London!

DIrections overview

This walk is fairly flat but does involve several sets of steps and some cobbled streets and narrow alleys. It is mainly on car-free, quiet streets and walkways.

Route details

Start /End London Bridge Station
OS Route  WALKING POST City of London
Difficulty Easy
Length 6 miles
Time  3 hours
Total ascent 318ft



SHORTER WALK  Tower Hill Station  loop 4.2 miles
Leaving out London Bridge and the river walk sections, start and finish from Tower Hill Station. This cuts the route down to just over 4 miles.

LONGER WALK  London Bridge to Waterloo  7.5 miles
Approaching the end of the walk, don’t turn into Hays Galleria but continue straight on along the Thames Path, taking in Southwark Cathedral, the Globe, Tate Modern and the South Bank Centre before finishing at Waterloo Station.



London Bridge Station, Fenchurch Street Station, Tower Hill (Gloucester court) , Cannon Street Station, Paternoster Square


On this route, you’re spoilt for choice, so we have just included some refeshment ideas with historical connections.
Ye Olde Watling 
29 Watling St, Greater, London EC4M 9BR
This pub dates back from 1668 and is built from Old Ships’ timbers. Christopher Wren used the upstairs rooms as offices during the construction of St. Paul’s Cathedral.

Ye Olde Cheshire Cheese
145 Fleet St, London EC4A 2BP
Just off Fleet Street on Wine Office Court, this pub was rebuilt shortly after the Great Fire of London. It’s known for its famous literary visitors including Charles Dickens, G.K.Chesterton, and Mark Twain.

Borough Market
8 Southwark St, London SE1 1TL
There has been a food market on this site since the 12th century, at least. The market is now full of lovely (but expensive!) speciality food stalls and restaurants.

The George Inn
75-77 Borough High Street London, SE1 1NH
London’s only surviving galleried coaching inn, Grade 1 listed with a large rambling layout and great open air courtyard.

Charterhouse Square

St Pauls Cathedral


Site of Dick Whittington's House

Postman's Park

Leadenhall Market

Tower Bridge & HMS Belfast

St Dunstans in the East

The Monument

Full directions

City of London walk directions - 6 miles

Underground – Take the Tooley Street exit.
Rail Take the escalators down to the lower level and leave via the Tooley Street exit between platforms 1 & 2.


  1. Turn left on Tooley Street and then cross the road and turn right at the junction to head across London Bridge
  2. Cross London Bridge, keeping to the Tower Bridge side. Just before the end of the bridge, take the metal spiral staircase on the right down to Thames walkway level. Turn right at the bottom of the stairs in the direction of the Tower of London, keeping the river on your right.
  3. Up the steps to your left, you’ll pass the Church of Saint Magnus the Martyr and further along, you’ll also walk past Old Billingsgate Market (now a corporate venue) before reaching the Tower of London.
  4. If you want to see the Traitors’ Gate, go around the Tower of London shop to get back to the riverfront. The Traitors’ Gate will be on the left-hand side after a short distance. To continue the walk, retrace you steps and head uphill past the shop and the first large tower booking office and then turn immediately left into paved Gloucester Court. There are toilets on your right.
  5. Ahead on the right you will see All Hallows by the Tower Church, founded in AD 675, which makes it likely to be the oldest church in the City of London.
    Continue past the church until you emerge onto Byward Street. Cross the road and continue straight down Great Tower Street. You will see the distinctive Walkie Talkie Building (otherwise known as the Fenchurch Building) ahead of you.
    Take the first left St Dunstans Hill, a cobbled lane and you will see black-gated entrance to St Dunstans in the East gardens on your right.
  6. Walk to the right of the church walls and emerge on the far side onto cobbled Idol Lane, Here, turn left and follow the lane around the right into St Mary on Hill. Turn left (you may see the Shard in the distance) and walk to the end on the road past the bollards, emerging on the busy Lower Thames Street.
  7. Turn right here and right again and you will see the Monument ahead of you. Pass through the bollards keeping the Walrus and the Carpenter pub to your right and walk straight on up towards the Monument.
    Just before the Monument you will cross Pudding Lane. To the right is where the Great Fire of London started in 1666.
  8. Keep walking straight on beyond the Monument up the cobbled street and you emerge on the busy King Williams Street, with London Bridge to your left. Cross straight over (you may need to cross at the traffic lights to your right.)
  9. Go straight down Arthur Street (this currently has building works on it) and turn first right up the cobbled Martin Lane and immediately left just before Old Wine Shades pub.
    Ahead, you will see some black railings.Go through them up the path between two low brick walls on Laurence Pountney Hill. At the end of the paved section, turn right up the cobbled hill and continue straight on to emerge onto Cannon Street.
  10. Turn left and continue straight on, past Cannon Street Station. Then, take the second turning to the left after Cannon Street Station into College Hill.
  11. Walk down straight across the crossroads and towards the church at the end. The last house on your left before the church is the site of Dick Whittingdons house. Turn right onto College Street and the right again onto Queens Place. Walk uphill and straight across the paved section emerging back onto Cannon Street.
  12. Cross straight over and continue down Queen Street and then cross Queen Victoria Street and take the second left up the paved Watling Street. Carry straight on and you will see St Paul’s Cathedral ahead of you in the distance.
  13. Continue straight on, crossing Bread Street and then joining New Change (the main road). Cross the road and keep straight on the walkway to the left of St Paul’s.
    Walk all the way round to the front of St Pauls, past the front steps. On the far side, you will see a large stone archway leading onto a square. This is Paternoster Square, a modern development which takes its name from Paternoster Row, which was once the centre of the London publishing trade, before it was devastated by aerial bombardment during the Blitz.
  14. Walk straight ahead keeping the column (a monument to both the Great Fire and the Blitz which destroyed the original Square) to your right and continue on up the paved Rose Street, emerging onto King Edward Street.
  15. Turn left. The road becomes Newgate Street and, just before the junction with Old Bailey and Giltspur Streets, you will see a plaque on the wall on your left marking the site of the Newgate Prison.
  16. If you head around the corner to your left, you’ll see the Central Criminal Court commonly referred to as the Old Bailey (named after the street on which it stands), with the Scales of Justice on its roof.
  17. Otherwise, turn right from Newgate Street, up Gilspur Street, keeping the Holy Sepulchre Church to your left.
    On the corner of Cock Lane in the left, look up and you will see the Golden Boy of Pye Corner.
  18. Walk straight ahead until the road opens up, with a small car park ahead of you. Keep to the right, walking straight down West Smithfield until you come to Smithfield Market, the very large building straight ahead.Cross the road and walk directly through the market on Grand Avenue.
  19. On the far side, turn right down Charterhouse Street which splits off to the left with a barrier for traffic. Continue along here until you come to Charterhouse Square. On your left is London Charterhouse.
  20. Turn right and walk diagonally through Charterhouse Square emerging on another road where you turn right, back towards Smithfield Market. Take the first left onto the paved Hayne Street with Smithfield to your right. At the end turn right onto Long Lane. Cross at the pelican crossing and then take the first left down the short paved alley (Rising Sun Ct). Ahead of you you will see the church St Bartholomew the Great. Turn right on Cloth Fair and to your right is 41 Cloth Fair, the oldest house in London.
  21. To the right of the church is a small churchyard with black railings. Go through the churchyard and take the steps down to Bartholomew Close. Back on the road, turn right and emerge onto Little Britain.
  22. Turn left and follow the road round to the right when it turns into King Edward street. You should see Postman’s Park on your left. Go through the gates into the park and walk straight through it. The memorial plaques are on your left in the middle of the square.
    Exit onto Aldersgate and turn immediately right. Cross the road and take the first left onto Gresham Street.
  23. On your left you will pass the churchyard of St John Zackary, destroyed by the Great Fire of London . Continue straight on until you see King Street on your right and a small passage to your left leading to a square and the Guildhall.
  24. After the Guildhall, carry on down Gresham Street and take a right down Princes Street. You’ll find yourself at the Bank of England. Bear right, continuing down Princes Street until you get to the junction. Across the junction is Mansion House, the home and office of the Lord Mayor of London.
  25. Turn left onto Cornhill – beyond the imposing Royal Exchange and then turn right into the paved Birchin Lane. At the end of Birchin Lane, turn left down Lombard Street and then, emerging onto Gracechurch street, turn left. Very soon, you will see the covered market of Leadenhall on your right.
  26. Walk straight through the market and out the other side onto Leadenhall Place. On your left, you’ll see the modern metallic Lloyd’s building, designed by Richard Rogers.
  27. Turn left onto Lime Street and you will see the Gherkin straight ahead. Next, turn right onto Fenchurch Avenue then first right down the paved Fen Court. At the end of the alley, turn left onto Fenchurch Street and then right onto Fenchurch Place and you will see Fenchurch Street Station at the end. (good for toilets).
  28. Immediately after the station, take the small steps down to the right into New London Street. Ahead of you, you will see St Olaves Church. This medieval church survived the Great Fire of London and is the burial place of Samuel Pepys.
  29. Turn left by the church and right down Seething Lane. On your left is a garden and the site of the navy office where Samuel Pepys lived and worked. Turn left into Muscovy Street and emerge at Trinity Street Gardens.
  30. Walk through the small park and cross Tower Hill and you are back on the paved area in front of the Tower of London. Turn immediately left on the raised walkway between Tower Hill and the moat of the Tower of London. Just before the tunnel under Tower Bridge Road, turn right up the steps and onto the bridge approach.
  31. Cross Tower Bridge and take the small staircase down to the Thames Path walkway. At the bottom turn left towards London Bridge.
  32. Continue by the river past HMS Belfast and turn left through Hays Galleria, which was originally a warehouse wharf for the port of London. You’ll emerge onto Tooley Street with London Bridge Station directly opposite.

Historical notes

City of London walk historical notes

Church of Saint Magnus the Martyr
One of Sir Christopher Wren’s most expensive churches, St Magnus the Martyr is the guild church of fishmongers and plumbers. Its beauty has drawn the attention of writers from Dickens to TS Eliot and its official burial ground is at Brookwood Cemetery (which you can walk around on another of our suggested routes!)

Look out for: the model of Old London Bridge inside the church

Old Billingsgate Market
This Grade II-listed building once housed the Billingsgate Fish Market which, in its heyday, was the largest fish market in the world. The market closed in 1982 and is now an events venue. The fish market has moved to the London Docklands.

Look out for: the Weathervane Fish on the roof

Tower of London
One of London’s famous attractions. A lot of kings and queens have lived here. There was once a zoo (there were frequent gifts of exotic animals – which eventually had to be moved to the Zoo as no one knew what to do with them). Now there are just ravens.

Traitors’ Gate
The name “Traitors’ Gate” has been used since before 1543. Prisoners were brought by barge along the Thames, passing under London Bridge, where the heads of recently executed prisoners were displayed on spikes. Possibly it would be better not to bring back the good old days.

St Dunstan in the East

Another Wren church – though originally built circa 1100 and almost destroyed in the Great Fire of London. The church was patched up after the fire, with a steeple designed by Wren but then it was bombed in WWII. The tower and steeple along with the north and south walls now enclose a public garden.

The Monument
The Monument to the Great Fire of London was built in 1668 to commemorate the Great Fire of London. It stands 202 ft west of the spot in Pudding Lane where the Great Fire started on 2 September 1666. Its height marks its distance from the site of the shop of Thomas Farriner (or Farynor), the king’s baker, where the blaze began.

For some extra exercise, you can climb the 311 steps to the top for 360 degree views over the City.

College Street – The House of Dick Whittington
Possibly the most popular London mayor of all time, Dick Whittington was a rich merchant and a philanthropist. He was first elected Lord Mayor in 1393 and then re-elected on three subsequent occasions. It’s unknown whether he ever owned a cat. But he did fund a 128-seat public lavatory, flushed by the Thames.

Watling Street
This is part of an historic route that once ran all the way from the Kent Coast to Shropshire. It was used by the Ancient Britons and was paved by the Romans to connect the port of Dubris (Dover) with Verulamium (St Albans) and Viroconium, a former Roman city in Shropshire. The A2 is partly made up this ancient highway and for certain stretches, the name ‘Watling Street’ is still used.

St Pauls
One of the most recognisable landmarks in the City of London, St Paul’s was Christopher Wren’s towering masterpiece. It’s the second biggest church building in the UK after Liverpool Cathedral and was the tallest building in London until 1963. Its dome is still one of the highest in the world.
Services held at St Paul’s have included the funerals of Admiral Nelson, the Duke of Wellington, Winston Churchill and Margaret Thatcher, jubilee celebrations for Queen Victoria and the wedding of Charles & Diana.

Newgate Prison
Newgate Prison was built in the 12th and remained in use for over 700 years, finally closing in 1902 and demolished in 1904. In the 18th century, public hangings took place here, drawing crowds of spectators. Thankfully, they were moved to a more private venue inside the prison in 1868.
Look out for: The gold scales of justice on the roof on the adjacent Central Criminal Courts of Justice,

This meat market has a history going all the way back to the 10th century. It’s been in continuous operation all that time and is now London’s only remaining wholesale market.

The London Charterhouse
This fascinating building was originally built on the site of a Black Death burial ground. Since then, it’s been a priory, a sumptuous mansion for use of Henry VIII’s most favoured courtiers, a school and an almshouse – a function it still retains today. It’s even suggested that football’s offside rule was invented here.

41/42 Cloth Fair
This is the only house in the City of London to have survived the Great Fire of London in 1666. It’s thought that it escaped the flames because it was enclosed within large priory walls. Inside the house, there are a set of leaded windows signed by some notable visitors including Winston Churchill and the Queen Mother.

Postman’s Park
So named because it overlooks the site of the former headquarters of the General Post Office, this is one of the largest open spaces in the City of London. It is home to the famous Watts memorial commemorating ‘heroic self-sacrifice’ and built in 1900 by Victorian painter and philanthropist GF Watts. The park also featured in the 2004 film Closer as an integral part of the plot.

The Guildhall has been used as a town hall for several hundred years, and is still the ceremonial and administrative centre of the City of London. The term “Guildhall” refers both to the whole building and to its main room, which is a beautiful, medieval great hall. Trials at the Guildhall have included those of Lady Jane Grey (the ‘Nine Days Queen’) and Henry Garnet, who was later executed for his involvement in the gunpowder plot.

The Bank of England
The central bank of the United Kingdom has been established here since 1694. It was privately owned from its creation until the government of Clement Attlee nationalised it in 1946. There are currently more than 400,000 bars of gold held in its vaults.

Leadenhall Market

This covered market dates back to the 14th century and was, 500 years later, given its ornate roof by Sir Horace Jones, who also designed Smithfield and Billingsgate Markets. It’s featured as Diagon Alley in the first Harry Potter film and has also made many other big-screen appearances.

Tower Bridge
There’s a persistent rumour that the American gentleman who purchased London Bridge in the 1960s and took it back to Arizona thought he was buying Tower Bridge which, let’s face it, is much prettier. This has been proven not to be true, but it’s still a fun story.