Despite the popularity of music festivals as a way through which to stage contemporary live music activity, a range of challenges exist in being able to stage such events in locales which are peripheral in geographical and market-share terms. This chapter examines the experiences of four music festival promoters who, between 1999 and 2009, were responsible for the staging of eight music festivals recognised as playing a vital role in the development and sustaining of the indie pop/rock music industry and scene of Perth, Western Australia. Perth is a city historically positioned as being on the periphery of national cultural activity in Australia due to its geographical isolation from other capital cities around the country and major regional centres in its own state. As this chapter explores, while the music festival format was looked to as a way of being able to capitalise on high investments of time, money and staging resources in order to stage live music in Western Australia, the promoters responsible faced a range of challenges in being able to sustain the high level of activity. This was a result of an increase in competition, staging costs and a saturation of the market.