Highgate Hill dates from circa 1386 when a new road from the City via Holloway had come into use as the main road going north.
The Bishop of London consented, on account of the “deepnesse and dirtie” passage of that way, to allow a new road to be carried through his park at Highgate, at the same time imposing a toll on all carts, wagons, and pack-horses. On the top of the hill, the gate which has given its name to the locality was erected . Until the fourteenth century there seems to have been no public road at all over the top of Highgate Hill.
Holloway Road and Highgate Hill became linked with the new North Road past the ‘highgate’. At the summit, Highgate sits atop a 426-foot hill.
Highgate Hill remains one of the steepest roads in London with its steepest gradient being the point where changes name to Highgate High Street. Dick Whittington is said to have sat upon a milestone on Highgate Hill on his way back to the family home in Gloucestershire. Inspired by the distant sound of Bow Bells, he turned again to find fame and fortune in London.
From the 16th century, houses began to form along Highgate Hill.
Travellers increasingly contributed to Highgate’s prosperity. The Black Dog, mentioned from 1735, was presumably the inn on Highgate Hill which later made way for St. Joseph’s retreat. Opposite stood the Crown, slightly below the later Old Crown which marked the southern end of Highgate village in 1774.
Highway robberies, many near the foot of Highgate Hill, led to the establishment of evening patrols from the Rose and Crown to Islington.
Until 1808, when Archway Road was built – providing a bypass – Highgate Hill was the main road up to Highgate village. The hill was particularly problematic for carts bearing heavy loads.
There were four other ways up the hill to Highgate – the present Dartmouth Park Hill (formerly Maiden Lane), Swain’s Lane, mentioned in 1481, Bromwich Walk, a bridle path connecting the top of Highgate West Hill with the bottom of Swain’s Lane in the 18th century but closed in 1904 and Highgate West Hill.
Highgate Hill was the route of the Highgate Hill Cable Tramway, the first cable car to be built in Europe. It operated between 1884 and 1909.
