In earlier centuries the two settlements were much smaller and known as East and West Shamblord; the East then being more significant settlement. The John Nash.

It is believed that the building of an 80 ton, 60 man vessel called Rat O'Wight on the banks of the river Medina for the use of Queen Elizabeth I of England|Elizabeth I sowed the seed for Cowes to grow into a world renowned centre of boat-building. However, seafaring for recreation and sport remained the exception rather than the rule until much later. It was not until the reign of keen sailor George IV of the United Kingdom|George IV that the stage was set for the heyday of Cowes as 'The Yachting Capital of the World.' In 1826 the Royal Yacht Squadron organised a three-day regatta for the first time and the next year the king signified his approval of the event by presenting a cup to mark the occasion. This became known as Cowes Regatta and it soon grew into a four-day event that always ended with a fireworks display.

In Cowes the 18th century house of Westbourne was home to a collector of customs whose son, born there in 1795, lived to become Dr Thomas Arnold, headmaster of Rugby School.

Northwood House was the home of the Ward family. It was donated under trust to the town in 1929, the grounds becoming Northwood Park. William George Ward was a close friend of the poet Tennyson and in whose memory the poet wrote six lines.

During the reign of Victoria of the United Kingdom|Queen Victoria, who made her summer home at Osborne by acquiring and rebuilding Osborne House, East Cowes was the subject of planned estate of grand houses, groves and parks. The scheme, not finding the finances it needed, was folded, but a few residences built in the early stages still survive to this day such as the former Albert Grove residences of Kent House and Powys House on York Avenue.

In East Cowes Norris Castle was designed in the Norman style by James Wyatt in the late eighteenth century. The building survives and today remains a private home. In 1798, the architect John Nash, began building his home, East Cowes Castle, where he later entertained the Prince Consort and other prominent guests. East Cowes Castle was notable for its gothic architecture|Gothic towers and turrets, and elaborate castellation. Nash died in 1835 and is buried in the tower of East Cowes Church which he also designed. East Cowes Castle was demolished during the 1960s, although the ice house remains and is visible in Sylvan Avenue.

Local industry in both Cowes and East Cowes has always centred on the building and design of marine craft, including the early flying boats, and sailmaking. It is also noted as the place where the first hovercraft was tested. East Cowes was also once home to the manufacturer Saunders Roe, who built the flying boat The Saunders-Roe Princess, as well as the Black Knight (rocket)|Black Knight rocket and the Black Arrow satellite carrier rocket. Another major employer is BAE Systems Integrated System Technologies (Insyte), which occupies a site at Newport.

West Cowes and East Cowes became a single urban district in 1933.

Its industry and proximity to Southampton and the Royal Navy's home at Blyskawica (itself built by White's), which put up such a determined defence that, in 2002, the crew's courage was honoured by a local commemoration lasting several days to mark the 60th anniversary of the event. In 2004 an area of Cowes was named Francki Place in honour of the ship's commander.

To celebrate the Silver Jubilee of the Elizabeth II of the United Kingdom|Queen's coronation in 1977, the main hangar doors of what was then the British Hovercraft Corporation (a successor to Saunders Roe) were painted with the world's largest image of the Union Jack.

Although respected as being the home of yachting in the UK, Cowes suffers from a severe lack of useable public slipways. The nearest, most convenient slipways being in East Cowes or the port of Yarmouth on the West of the Island.

Famous residents