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For some 900 years the land north of today's Docks was a walled compound, initially designed to keep people out, then keep them in. What was until its closure in 2013 Gloucester Prison stood on the site of an early 12th century Norman castle. The siege of Gloucester Castle during the Second Barons' War in 1263 and its seizure in 1264 and again in 1265 prompted the King to clear the area around the castle. Several properties were demolished to deny cover to any future besiegers.

The bare land thus created is preserved today in name by Bearland, the street that links Quay Street with Longsmith Street. The latter was the centre of Gloucester's once important iron-smith industry. Ore was delivered from the Forest of Dean to The Quay, the city's port facility before the early 19th-century construction of Gloucester Docks. Gloucester smiths supplied weapons and utensils to King Henry II in the years 1171–1173, when the king invaded Ireland and faced revolt by his sons. They also provided materiel for the crusades and, in the first half of the 13th century, to King Henry III for his campaigns in Wales and France.

By the 18th century the iron-smith industry had declined. Longsmith Street became a fashionable residential area and development began to encroach on the bare land. Today, the Bearland area is the city's civic centre, the location of its courts, Shire Hall and main police station.

Castle and prison

By the 18th century only the inner keep of Gloucester Castle remained, and its sole purpose was to serve as the city's prison. It was a wretched, neglected place, the subject of calls for prison reform which culminated in 1787 with its demolition and the construction in its place of Gloucester Prison. Although that prison is itself now being dismantled after its closure in 2013, the five listed sites – including the central cell block and prison chapel, built 1844–1850 and incorporating the c.1789-built gatehouse – are undergoing the slow regeneration into a residential quarter.

The c.1850-built governor's house on Commercial Road incorporates a c.1789-built tower on the perimeter wall. A later section of perimeter wall, erected in 1826 when the prison was extended, still runs along the pedestrianised Barbican Road. At the apex of the triangular extension around which this wall was built is another cell block, built in 1826 as a debtor's prison. The final listed site is the 1826-built outer gatehouse, which sits close to where the main gate into the castle once stood. Until 1864, prisoners sentenced to death were hanged from gallows erected on the roof of the gatehouse.

At the far end of Barbican Road is Bearland, across which road is the institution responsible for populating the prison; what is today Gloucester Crown Court was built in 1816 as the assize, quarter session and county courts. The building was part of the Shire Hall development, designed by Sir Robert Smirke, who also designed what became known as the Judges Lodgings at the city's Spa development and the extension of the British Museum in London.

From bare land to Bearland

On the corner opposite the court, where Bearland becomes Longsmith Street, is Bearland House. This townhouse was built c.1735–1740 on the site of an earlier, late 17th-century or early 18th-century house. It was extended c.1750 with the addition of wings either side of the front.

In 1764 the house was purchased by Samuel Hayward, a Justice of the Peace and High Sheriff of Gloucestershire. The purchase included the bare land behind (extending south to Commercial Road between Barbican Road and Ladybellegate Street), which became formal gardens and orchards.

In 1856 the house became a depot for the Gloucestershire militia. In 1899 the entire estate was sold to the City, which transformed the gardens into the City Electricity Works (now a building site). The west wing was demolished c.1912 and a fire station erected in its place for the city's newly formed fire brigade. The unlisted fire station building still exists, though it ceased to be a fire station in 1956.

In the 20th century Bearland House served variously as a school building for what later became the Denmark Road High School, a solicitors' office and, between 1915 and 1972, the Gloucester headquarters of the Post Office Telephone Service. It currently serves as a factory for the Emma Willis luxury clothing business.

Opposite Bearland House, the Saxon-origin Berkeley Street follows the original line of the wall erected by the Romans to mark the western limit of their colonial city. The west side of the street is lined with three listed buildings, all of them originally built in the late-18th century as townhouses. No. 20 now serves as flats, while Langham House and No. 16 are offices.

Ladybellegate

On the other side of the east wing of Bearland House on Longsmith Street is Bearland Lodge, built c.1720 as a townhouse for a barrister from Apperley. A pediment depicting the legend of Perseus and Medusa is likely to have originally adorned Ladybellegate House, a little farther up Longsmith Street.

Ladybellegate House was built c.1704 by Henry Wagstaffe, son of a Civil War Royalist sympathiser/former mayor of Gloucester. From 1732 to 1740 and again from 1743 to 1772 the house was rented by the Raikes family. Robert Raikes the elder was the successful proprietor of the Gloucester Journal, and his son, also called Robert, became famous as a pioneer of the Sunday School movement. He also championed in the newspaper he inherited from his father the cause of prison reform that would eventually see Gloucester's dilapidated castle-prison replaced by the purpose-built facility a decade before his retirement.

In the 20th century the house served for a while as a health centre. It was bought by the Post Office and later sold for £1 to the Gloucester Civic Trust. After restoring the property, the Trust sold it and used the proceeds to fund Gloucester Historic Buildings Ltd, a joint venture with Gloucester City Council to protect and preserve historic buildings and monuments.