The use of Roger's Field as a potential site for a ballroom and indoor event venue was discussed by the Town Advertising Association in 1914, however the outbreak of the First World War postponed the development.

The current Winter Gardens Pavilion was designed in 1924 in a collaboration between landscape architect Thomas Hayton Mawson and town surveyor Harry Brown.

A height restriction imposed by a covenant relating to the nearby Royal Hotel compromised the design and resulted in a sunken ballroom and a small domed roof.

[1] During the Second World War, Weston-super-Mare was hit heavily by Luftwaffe bombing, and it has been reported, without direct evidence, that the Winter Gardens may have been damaged.

[8] In January 2015, North Somerset Council agreed to sell Weston-super-Mare's Winter Gardens Pavilion to Weston College for the nominal fee of £1.

[9] The sale was part of the council's plan to regenerate Weston-super-Mare's town centre and the college intend to turn the 1989 extension into a law and professional services academy.

[17][18] Catherine Gibbons, a town Councillor, announced in September 2015 that she would attempt to have parts of the building protected for community use under the Localism Act 2011,[19] but the listing was rejected by the council.

[24] Proposals for the Winter Gardens' redevelopment preserved the historic 1920s portion of the building for public use, and included the refurbishment of the ballroom and kitchen.

[28] The last scenes of The Remains of the Day, a James Ivory film of 1993, were shot at locations in the town including the Grand Pier and the Winter Gardens.