The inconvenience of the access to Edinburgh by the great London road was, by the early nineteenth century, long a subject of general regret. In entering the city from this quarter, the road lay through narrow and inconvenient streets, forming an approach in no way suited to the general elegance of the place. In 1814, however, a magnificent entrance was commenced across the Calton Hill, between which and Princes Street a deep ravine intervened, which was formerly occupied with old and ill-built streets. In order to connect the hill with Prince's Street, all these were swept away, and an elegant arch, called Regent Bridge, was thrown over the hollow, making the descent from the hill into this street easy and agreeable.
Regent Bridge, designed and constructed under the direction of Robert Stevenson, was begun in 1816, and finished in 1819. The arch is semicircular, and fifty feet wide. At the north front it is forty-five feet in height, and at the south front sixty-four feet two inches, the difference being occasioned by the ground declining to the south. The roadway is formed by a number of reverse arches on each side. The great arch is ornamented on the south and north by two open arches, supported by elegant columns of the Corinthian order. The whole property purchased to open the communication to the city by this bridge cost £52,000, and the building areas sold for the then immense sum of £35,000. The street along the bridge was called Waterloo Place, as it was founded in the year on which that memorable battle was fought.