The medieval period, however, Dundee was second only to Edinburgh in terms of commercial prosperity. Most early trade was by sea and Dundee was ideally located on shipping routes to and from the Baltic and North European ports due to being closer than Edinburgh by two days sailing. The earliest harbour is thought to have been at Gellatly Street/Seagate junction, the port had moved westwards by the 16th Century to a point close to the current High Street at Whitehall Crescent.
From here the harbour developed during the 17th and 18th Centuries. By the 1830s when flax gave way to jute, Dundee changed from a trading port to the world centre for the jute processing industry and the city rapidly expanded.
Thomas Telford was appointed to improve the harbour facilities and built the King William IV Dock and the West Graving Dock, on the site of the old tidal harbour, plus a new tidal harbour to the south. The development of the dock continued for the next 100 years, with Earl Grey Dock formed and Victoria and Camperdown Docks added to the east moving the city further away from the waterfront.
The railways followed soon after and by the end of the 19th Century, the first signs of decline were apparent and the docks were no longer heavily used. In 1911, the City Architect, James Thompson prepared designs for a new Civic Centre on the site of the Waterfront, but the commencement of the World Wars meant that these proposals were never implemented.
In the 20th Century, the most significant factor which determined Dundee's relationship with the Waterfront was the siting on the northern landfall of the Tay Road Bridge. Olympia Leisure Centre and Tayside House were then built in the 1970s - the resultant effect was the loss of the harbour and the serverance of the waterfront from the city.