The area around Winchester has been inhabited since prehistoric times, with three Iron Age hillforts, Oram's Arbour, St. Catherine's Hill, and Worthy Down all nearby.

In the Late Iron Age, a more urban settlement type developed, known as an oppidum, although the archaeology of this phase remains obscure.

[7] The Roman account of continental invaders has been challenged in recent years with scientific studies favouring a gradual change through increased trade links rather than migration.

[11] An etymology connected with the Celtic word for "white" (Modern Welsh gwyn) has been suggested, due to Winchester's situation upon chalk.

Although in the early years of the Roman province it was of subsidiary importance to Silchester and Chichester, Venta eclipsed them both by the latter half of the second century.

The city may have functioned as a centre for a religious community or a royal palace, as they continued to use the Christian cemeteries established in the Roman period.

Between 476 and 517 AD, the town and surrounding areas seems to have been fortified by several Jutish settlements[20][21] [a] and to have operated as part of a larger polity.

The present form of the city dates from reconstruction in the late 9th century, when King Alfred the Great obliterated the Roman street plan in favour of a new grid in order to provide better defence against the Vikings.

The three minsters were the home of what architectural historian John Crook describes as "the supreme artistic achievements" of the Winchester School.

[26][27][28][29] Martin Biddle has suggested that Winchester was a centre for royal administration in the 7th and 8th centuries, but this is questioned by Barbara Yorke, who sees it as significant that the shire was named after Hamtun, the forerunner of Southampton.

[33] A statue of Licoricia of Winchester, described as "the most important Jewish woman in medieval England", located in Jewry Street, was unveiled by the then Prince of Wales on 10 February 2022.

[34][35] The City Cross (also known as the Buttercross) has been dated to the 15th century, and features 12 statues of the Virgin Mary, other saints and various historical figures.

When his workmen arrived to dismantle the cross, they were prevented from doing so by the people of the city, who "organised a small riot",[36] and they were forced to abandon their task.

The agreement with the city was cancelled and Dummer erected a lath and plaster facsimile, which stood in the park for about sixty years before it was destroyed by the weather.

[38] The city walls were originally built in the Roman period covering an area of around 138 acres (56 ha), and were rebuilt and expanded in sections over time.

[41] Three notable bronze sculptures can be seen in or from the High Street by major sculptors of the 19th and 20th centuries, the earliest a monumental statue of Queen Victoria, now in the Great hall, by Sir Alfred Gilbert (also known as the sculptor of 'Eros' in London's Piccadilly Circus), King Alfred, facing the city with raised sword from the centre of The Broadway, by Hamo Thornycroft and the modern striking Horse and Rider by Dame Elizabeth Frink at the entrance to the Law Courts.

[42] While staying in Winchester from mid-August to October 1819, the Romantic poet John Keats wrote "Isabella", "St. Agnes' Eve", "To Autumn", "Lamia" and parts of "Hyperion" and the five-act poetic tragedy "Otho The Great".

Unlike parishes, members are not directly-elected, but instead are the city councillors who were elected to the respective wards, who sit ex officio on the town forum.

Winchester is currently represented in the House of Commons by Danny Chambers, of the Liberal Democrats, who in the 2024 General Election beat Flick Drummond, the Conservative candidate, by 13,821 votes (a margin of 24.2%).

The office of Mayor of Winchester currently exists as a ceremonial role, but dates back at least as far as the late 12th century.

[55] The mayoral term length is currently one year, and is the chair of Winchester City Council, covering the wider district since 1974.

Entrance for pedestrians to the North garth of the cathedral is via the Norman arches of Saint Maurice's tower, in the High Street.

[59] The almshouses and vast Norman chapel of the Hospital of St Cross were founded just outside the city centre by Henry de Blois in the 1130s.

[60] Local items featured include the Roman Venta Belgarum[61] gallery, and some genuine period shop interiors taken from the nearby High Street.

Other places of cultural interest include the Westgate Museum (which showcases various items of weaponry), and the Historic Resources Centre, which holds many records related to the history of the city.

[66] A series of 24 bollards on the corner of Great Minster Street and The Square were painted in the style of famous artists, or with topical scenes, by The Colour Factory between 2005 and 2012 at the behest of Winchester City Council.

[85] Local, rural and Park and Ride bus services are provided by Stagecoach South, who run to Andover, Alton, Basingstoke, Petersfield, Romsey and Fareham.

There is a heavily populated Victorian prison, HMP Winchester, opposite the hospital, on the B3040 heading up west from the town centre.

[93] Since 1974 Winchester has hosted the annual Hat Fair, a celebration of street theatre that includes performances, workshops, and gatherings at several venues around the city.

The weekly paid-for Hampshire Chronicle, which started out in 1772 reporting national and international news, now concentrates on Winchester and the surrounding area.