The festival was founded in 1985 by Sheldon Wilner and Dick Finkel with the intention of bringing the art of street performance to Edmonton’s downtown region.

The "Troupe de Jour" program brings select artists together every night during the festival for an original variety show that combines the unique talents of the performers involved.

"Be Your Own Busker" is an educational series aimed at teaching both children and adults some of the basics of street performance, like juggling and making balloon animals.

[6] In 1987, StreetFest centralised and hosted all of its artists in Sir Winston Churchill Square, where the festival is still held today.

This proved fruitful, as it brought the visiting artists into closer proximity to one another, and the next year, in 1988, many of the performers got together to throw an impromptu variety show called "Late Night Madness," a tradition that has continued ever since, except 2020.