The structural transformation of retail is challenging for many small cities. Rather than seeing the retailer as a sole player, this article considers retail in small cities to be shaped in a retail eco system consisting of many different actors besides retailers such as municipalities, landlords, business/city organisations, customers/citizens. The key contribution of the article is to provide new perspectives on the challenges and management of retail in small cities by applying a metaphor from the culture and fine arts sector, orchestration. The article is based on a combination of in-depth interviews and participant observation at three small cities in Sweden. In total, 38 interviews have been conducted with representatives of retailers, municipality, business/city associations and landlords. The general aspects of retail eco system as an orchestra are presented according to Klein and Kozlowski, (2000) multilevel constructs: compiled (bottom-up), composite (top-down) and emergent (culture, history). Thereafter, a number of orchestration techniques, structured around Pine and Gilmore, 1999 dimensions of experiences are presented. The article shows that the future of retailing in small cities is not merely dependent on the retailers, but on collaborations with other retailers, landlords and municipalities. An understanding of consumer culture and development of entrepreneurship culture and networks is crucial for survival and prosperity. Furthermore, rather than copying strategies developed both in and for metropolitan areas, there is a need to build on and strengthen the characteristics of the local retail eco system and the community brand identity.