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Chester retains many elements of the grid-like layout of Roman Chester within the City Walls, ouside of which it had barely expanded by the the time of an 1825 Map. After 1825, the first major departure from the rectilinear street plant was Grosvenor Road, leading to the Grosvenor Bridge, later came City Road to serve Chester Station and later still the Inner Ring Road.

Looking down Upper Bridge Street in 2015 with the High Cross in the foreground and Eastgate Street to the left. This wss the site of the headquarters of the garrison of Roman Chester. The building left of center is by Thomas Meakin Lockwood (1888) one of the architects who developed the "Chester Look". The High Cross was broken up at the end of the siege of Chester in the Civil War and some surviving parts only restored to its ancient original site at the intersection of the city's main streets in 1975, after an absence of some 329 years.

The compass of directional expansion of Chester was determined by trade. In Roman Chester and later, in the Medieval, came growth along Foregate Street to be the first to grab trade entering the city from the east. With the "Canal Mania" around 1770 and the difficulties of the silting of the River Dee, Chester grew to the west, then in the 1840's the railway brought growth to the north.