York Way long formed the boundary between the parishes of St. Pancras and Islington. For its entire length York Way now forms the boundary between the London Boroughs of Islington and Camden. It only became York Way in the mid twentieth century but it is one of the most ancient roads in the north of London.

York Way was named ’Mayde Lane’ (1467) and ’Maiden Lane’ (1735) (commemorated in the Maiden Lane Estate, Maiden Lane Bridge - over the Regent’s Canal and the former Maiden Lane railway station). It became York Road in the 19th century, and the current name was adopted in 1938.

The historian Camden says, "It was opened to the public in the year 1300, and was then the principal road for all travellers proceeding to Highgate and the north." It was formerly called ’Longwich Lane’, and was generally kept in such a dirty, disreputable state as to be almost impassable in winter, and was so often complained of that the Bishop of London was induced to lay out a new road to Highgate Hill, so that a carrier might get to the north by avoiding Longwich Lane.

"The old and anciente highwaye to High Barnet, from Gray’s Inn and Clerkenwell," writes John Norden, in his ’Speculum Britanniæ’, "was through a lane to the east of Pancras Church, called Longwich Lane, from whence, leaving Highgate on the west, it passed through Tallingdon Lane, and so on to Crouche Ende, thence through Hornsey Great Park to Muswell Hill, Coanie Hatch, Fryene Barnete, and so on to Whetstone. This anciente waye, by reason of the deepness and dirtieness of the passage in the winter season, was refused by wayfaring men, carriers, and travellers, in regard, whereof, it is agreed between the Bishop of London and the countrie, that a new waye shall be laide forthe through Bishop’s Park, beginning at Highgate Hill, to leade directe to Whetstone, for which a certain tole should be paid to the Bishop, and for that purpose has a gate been erected on the hill, that through the same all travellers should pass, and be the more aptly staide for the tole."

At the southern end, after the main line King’s Cross station was the smaller suburban York Road station, with services both north and to Moorgate.

After the canal the road is adjacent to the former Kings Cross goods station and, standing on the corner of Bingfield Streetand, the red tiled surface building of the disused York Road Underground station is located. The station was closed in 1932 and was served by the Piccadilly line.

Between here and the former Maiden Lane railway station the road was rebuilt in the 2000s to enable the tunnel entrance for High Speed 1 to be constructed.

Near the northern end of the road was the Metropolitan Cattle Market; now the Market Estate and Caledonian Park.

The modern road passes the new Kings Place development, Bingfield Park, crosses the Regent’s Canal, and runs alongside the King’s Cross redevelopment area.