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There is evidence to suggest that a quay was located on the Old Severn, a now vanished channel of the River Severn, at St. Oswald's Priory. When that silted up a new quay, first recorded in 1390, was established on the east channel of the Severn in the area where the Old Custom House is now located, near the entrance to Quay Street.

The quay handled goods carried to and from Gloucester by small boats that navigated the Severn from Worcester and Shrewsbury in the north to Bristol and Chepstow in the south. In 1580 Queen Elizabeth I granted Gloucester port status, allowing the city to trade directly with foreign ports. The quay was designated the new port's principal landing place, and a customs house was built the next year, possibly on the site of the early 18th-century Old Custom House that still survives today. Gloucester became the nation's most inland port, a distinction it retained until the Port of Goole was opened in 1826.

By the early 18th century, the quay and associated buildings extended south to just short of today's Barrack Square, which runs down the side of the old prison on the former site of Gloucester Castle. By the end of the century hundreds of boats were trading each year at Gloucester and larger ships began to bring wine from Spain and Portugal.

The larger vessels could navigate up the Severn only on the highest tides. Most of them chose to dock at Bristol, where cargoes were transferred to smaller boats that could more easily manage the passage up the river.

The quay declined in importance as the Docks were developed. The river wall was extended to Gloucester Lock in 1937 as part of a road improvement scheme. Further road widening in the 1960s brought trading at the quay to an end and left only the Old Custom House as a reminder of this patch of Gloucester's maritime trading heritage.

Docks and Canal Development

To improve the city's maritime trade prospects, work was begun both on enlarging the port and bypassing the difficult-to-navigate Severn with a canal from the city to Berkeley. Digging began in 1794, but by 1799 the money had run out. Gloucester Lock – double chambered in its initial construction – the main basin and just four miles of canal to Hardwicke had been completed. The main basin lay dormant until 1812, when the completion of the horse-drawn Gloucester and Cheltenham Tramroad encouraged vessels to bring coal into the docks. The tramroad is commemorated today by replica wagons outside Albion Cottages in Victoria Dock.

In 1814 a ship-builders yard opened in the main basin, followed in 1818 by a dry dock. The latter was rebuilt in 1837 and supplemented in 1853 by a larger dry dock, both of which remain in use by T. Nielsen & Company, whose specialist maintenance skills attract historic sailing vessels to the Docks.

A government loan allowed construction to resume in 1818. The route was shortened, the plan now to connect to the Severn at Sharpness rather than Berkeley, and junction was made with the Stroudwater Navigation at Saul in 1820 before the money ran out again. More government money enabled construction to resume for the last time in 1823, though repaying this debt would burden the canal company for the next half century. In anticipation of increased traffic as the canal neared completion, the barge arm was dug off the main basin at Gloucester in 1825.

What was the world's longest, deepest ship canal was finally opened 26 April 1827. The same year, the canal company built the first of the warehouses, North Warehouse. Over the following decades more followed, privately built but to a similar design as mandated by the canal company.

Gloucester prospered as a centre of grain and timber import, and as the Docks flourished capacity was expanded. In 1836 the canal south of Llanthony Bridge was widened and Baker's Quay established by entrepreneurs Samuel Baker and Thomas Phillpotts, slaveowners whose fortunes were derived in part from compensation they received following the abolition of slavery in 1833. In 1849 another basin, Victoria Dock, was excavated next to the main basin, along which Victoria, Albert and Britannia Warehouses were built in 1849, 1851 and 1861 respectively. All three warehouses are still standing today, though Britannia was rebuilt after being destroyed by a fire in 1987 and is not listed by Historic England.

The arrival of the railways in the mid-19th century saw the end of the Gloucester and Cheltenham Tramroad. Two large rail yards were laid out in the docks: one in High Orchard behind Baker's Quay; the other one opposite, across the canal at the newly built Llanthony Quay (now the site of the Gloucestershire College campus).

The Llanthony Quay rail yard was the terminus of a branch line off the Gloucester and Dean Forest railway. The branch was laid across Alney Island from the main line farther north to bring coal from the Forest to the Docks. It crossed the Severn by a hydraulically operated swing bridge, built in 1852. Its replacement, built in 1899, still stands today as a listed site, albeit barricaded and in a sorry state of repair.

Development of the Docks slowed after the 1860s as ships grew beyond the capacity of canal and docks. Although Gloucester Lock was remodelled in 1892 into its current single large chamber form, the canal company focused its attention on the development of port facilities at Sharpness. The slow decline of the Docks as a commercial port accelerated after the Second World War as the road network became the dominant form of transport, particularly for timber. Although the canal itself remained commercially viable thanks to the transport by barge of petroleum, by the 1960s, warehouses and railways at the Docks were being dismantled, followed the next decade by the demolition of some of the smaller buildings.

Pleasure craft began to supplant commercial vessels as the main users of the Docks in the 1970s. Grain shipments ceased when Albert Mill closed in 1977, and the last significant commercial traffic disappeared from the canal in the 1980s as the transport of petroleum shifted to pipelines. In the mid 1980s North Warehouse was refurbished as offices by the city council, the start of the regeneration of the docks as the retail, residential and leisure area it is today. Other than the demolition of the West Quay warehouses in 1966 (replaced now by 21st-century apartment blocks), and the loss to arson of Britannia Warehouse in 1987 and the main part of Provender Mill in 2018, the repurposed Docks fundamentally retain the architectural character of the 19th-century port.

That regeneration is ongoing. In April 2020 demolition work was begun on the 1893-vintage Downings Malthouse No. 2 at Baker's Quay, the facade of which will be retained by the apartments it will become. In 2023 planning permission was granted for a ten-storey residential tower on the site of a concrete silo that had replaced Downings Malthouse No. 1 in the 1950s. Their neighbours – the 1867-built rail transit shed and 1901-vintage Downings Malthouse Extensions – currently lie derelict on the canal side; in some ways the least opaque of windows on the Docks' past as they await their turn to be reborn into the 21st century.

There are two museums at the docks, both highly recommended. The National Waterways Museum Gloucester at Llanthony Warehouse tells the story of the docks and canal. The Soldiers of Gloucestershire Museum at the former Customs and Excise office tells the story of the county's military heritage.

Two miles down the canal is one of several listed mileposts that show the distance to Gloucester on one side of the triangular post and the distance to Sharpness on the other. Another half mile on at Rea Bridge is the first of a handful of listed bridge-keeper's cottages that still survive along the canal, all built by the Gloucester and Berkeley Canal Company to the same design.