Live it Vintage took place in the High Street and inside the Nicholson's Centre on Saturday, bringing to life popular culture from the 1920s up to 1980s.
Music featured everything from 1950s rock 'n' roll to a ukulele player and DJs before models took to the catwalk for a fashion show.
More than 20 stalls sold clothes, cupcakes, and vintage gear, while a make-up artist created the look from different eras and pictures were taken in a retro photo booth.
A 1960s VW Variant could also be seen parked up in the High Street, as people flocked to sample the new festival.
Organiser Samantha Claridge, of Wooton Way, a born and bred Maidonian, said the festival was inspired by the town's Mary Portas grant bid, which she was part of.
The former Cox Green School pupil said: "The idea came up when we were applying for the Mary Portas grant as I have always had an interest in retro.
"Hopefully we will run it two times a year like Art on the Street and also do other events to tie in once a month."
Samantha, who owns Sew Crafty in the High Street, said Marie Leonard, organiser of Art on the Street, and town centre manager Steph James were a big part of the organisation.
The event was arranged by non-profit organisation Live it Events in conjunction with the town centre management team.
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