The initial stretch of the road was St John Street which begins on the boundary of the city (the site of the former West Smithfield Bars), and runs through north London.
Less than a hundred metres up St John Street, into Clerkenwell, stood Hicks Hall, the first purpose-built sessions house for the Middlesex justices of the peace.
When the General Post Office at St Martin's-le-Grand, in the historic Aldersgate ward, was built in 1829, coaches started using an alternative route, now the modern A1 road, beginning at the Post Office and following Aldersgate Street and Goswell Road before joining the old route close to the Angel.
A road forked to the left at the bridge in Boroughbridge to follow Dere Street, and Scotch Corner to Penrith and on to Glasgow.
[6] The highwayman Dick Turpin's flight from London to York in less than 15 hours on his mare Black Bess is the most famous legend of the Great North Road.
It is claimed that Nevison, in order to establish an alibi, rode from Gad's Hill, near Rochester, Kent, to York (some 190 miles (310 km)) in 15 hours.
The Winchelsea Arms, an inn on a long straight section of the Great North Road near Stretton, Rutland, was reputed to be another haunt of Dick Turpin.
[7] In literature Jeanie Deans of Sir Walter Scott's novel The Heart of Midlothian travels through several communities on the Great North Road on her way to London.
B. Priestley novel The Good Companions mentions the road, which represented to protagonist Jess Oakroyd (a Yorkshireman) the gateway to such 'exotic' destinations as Nottingham.
The Lord Peter Wimsey short story "The Fantastic Horror of the Cat in the Bag" by Dorothy L. Sayers features a motorcycle chase along it.
In Cassandra Clare's Clockwork Princess, the third volume of The Infernal Devices trilogy, Will Herondale takes the road after leaving London on his way to Wales to find Tessa Gray.