Geoff Stephens was a staff songwriter who was fond of the Twenties style of music. He had a calendar with a photograph of the Winchester Cathedral in his office and being a songwriter he composed a song about the building. To ensure that the sound he desired was achieved he hired session players dubbed The New Vaudeville Band to record the music tracks, complete with a Rudy Vallée soundalike, John Carter, singing through his hands to imitate a megaphone sound. "Winchester Cathedral" was released in late 1966 by Fontana Records, and surprisingly, became an instant hit, reaching Number Four in his native country and the top slot in the US. With Fontana trying unsuccessfully to recruit the Bonzo Dog Doo-Dah Band, Stephens had to hastily assemble a group of musicians to tour in support of the song. They toured extensively in the UK and America then had an extended engagement at The Aladdin Hotel in Las Vegas. They followed up with "Peek-a-Boo" and "Finchley Central" but gradually faded from the charts.
Singer Rudy Vallée, whose voice and style the original recording imitated, did his own cover of the song in 1967 when he was in his late 60s, but it did not chart.