When English settlers arrived in the early 1600s, two Native confederacies divided central Virginia at the fall line of the James. West of the falls, the Manakins - part of the Monacan Indian Nation - controlled the southern Piedmont. East of the falls, the Powhatan Confederacy, led by Wahunsonacock, held the Tidewater. The earliest European foothold here was Henricus in 1611, where Falling Creek meets the James. Eight years later, Virginia Company settlers built the Falling Creek Ironworks - one of the earliest industrial enterprises in English America. The Anglo-Powhatan Wars of 1622 to 1646 ended with the Powhatan Confederacy broken and Opchanacanough dead. After Bacon's Rebellion in 1676, Cockacoeske signed the Treaty of 1677, accepting tributary status for the surviving Virginia tribes in exchange for protection and reserved lands. By 1699 the Manakins had largely left their settlements, and the English allotted the south bank to French Huguenot refugees, who founded Manakintown.

After Benedict Arnold's Revolutionary War raids destroyed the port of Warwick in 1781, the smaller settlement of Manchester took over the role of Richmond's south-bank port. The 1788 Mayo Bridge connected it across the falls to Richmond. Manchester sat at a strategic point: water access east via the James, road access west toward the Midlothian coalfields, and rail access soon to come. The 1804 precursor to the Midlothian Turnpike ran from Manchester west to Falling Creek, where the Black Heath coal mines and the Bellona Arsenal needed a way to get their product to ships. The 1831 Chesterfield Railroad - one of the first railroads in America - hauled coal directly from the Chesterfield pits to Manchester wharves. The Richmond and Petersburg Railroad followed in 1838, then the Richmond and Danville in 1853. Manchester briefly served as Chesterfield's county seat after the Civil War from 1870 to 1876. In 1874 it voted to become an independent city. In 1910 it agreed to be annexed by Richmond, on the condition that a free bridge be built across the river.

The Manchester Bridge - the free bridge the city demanded as a condition of annexation - opened in 1911. Westham Bridge followed the same year. The Nickel Bridge (originally a toll bridge, hence the nickname) opened in 1925. The Lee Bridge opened in 1933, also as a toll. Each new bridge stitched more of the south bank to downtown. The Jefferson Davis Highway opened in 1927 and within a decade a 1940 WPA guide called it 'a glittering midway' of tourist cabins and neon. The DuPont Spruance plant opened in 1929 on the old Ampthill plantation site, producing rayon and cellophane. After World War II, Southside boomed. The Bellwood military supply center had been built in 1942. Southside Plaza opened on Belt Boulevard in 1957-58. The Richmond-Petersburg Turnpike, predecessor to I-95, opened in 1958. Chippenham Parkway was completed in 1967. Powhite Parkway opened in 1973. The suburbs reached west into Chesterfield County so quickly that subdivisions named themselves before they were finished.

In 1970, Richmond annexed another 23 square miles of Chesterfield County, pushing its border out to the Chippenham Parkway. The annexation included historically Black neighborhoods that the city was eager to add to its tax base - and excluded white suburbs the city's leaders preferred to leave in the county. The motivations were openly racial: by diluting Black voting power within Richmond, white-led city government hoped to preserve its majority. Civil rights advocates sued. The case, City of Richmond v. United States, reached the Supreme Court in 1975. The Court ultimately upheld the annexation but ruled it had unlawfully diluted Black voting strength; Richmond was required to redraw its council wards into a system that gave the city's Black majority a fair share of seats. A moratorium on further annexations followed. The city's borders are still essentially where the 1970 annexation left them. Bon Air and the DuPont Ampthill property stayed in Chesterfield, as the negotiation demanded.

The Powhite Parkway Extension opened in 1988, connecting Chippenham out to the new Route 288 beltway, which by 2004 had closed a full ring around Richmond - crossing the river at the World War II Veterans Memorial Bridge. The Pocahontas Parkway, opened in 2002, gave Southside direct access to I-295 and Richmond International Airport. Stony Point Fashion Park opened in 2003. The 'For Members Only' bumper stickers faded. The historically Black neighborhoods of Swansboro and Blackwell - and what's now called Old Manchester, where tobacco warehouses and brick storefronts from the nineteenth-century port survive - have become subjects of fierce debates about gentrification. Historic tax credits have turned old buildings into apartments. New residents have moved in. Older residents, many of them Black, face rising rents and displacement. Forest Hill Avenue has seen its own renaissance, with the South of the James farmer's market drawing weekend crowds in Forest Hill Park. The south bank has finally arrived at being part of the city it crosses the river to reach. What it does with that status is still being decided, neighborhood by neighborhood, lease by lease.