Annual trading fairs have been an important part of social, economic, and cultural life in small towns across Turkey. Fairs (panayır, in Turkish, from the Greek panegyri) provide a rare opportunity for shopping and entertainment to the residents of small towns and villages. Women have always played vital roles in the fairs, not only as consumers, but also as fair merchants, vendors, and entertainers. The roles of women, especially Roma women, have been particularly pronounced in the entertainment sector of the fairs, from the singers and dancers in the “entertainment tent” to operators of the ring toss, penalty kicks, and the various games of chance. The earlier scholarship on the fairs mostly focused on the economic dimensions of the Ottoman-era fairs. In recent decades, scholarly interest in the fairs has grown some, led by a small number of geographers, folklorists, and historians. However, the role of women and gender in the fairs, especially the role of female Roma entertainers, is yet to be fully explored. Two recent articles in the Journal of Ottoman and Turkish Studies Association have touched on the subject within the context of the early republican history, but these studies did not extend beyond the 1940s. Drawing primarily on oral historical and ethnographic research conducted at five separate fairs in Thrace, the Western Black Sea, Marmara, and Aegean regions, this paper explores the place of women, particularly the role of female Roma entertainers, within the changing landscape of Turkey’s panayırs. The ethnographic method allows for documenting how the panayır entertainments function with the Roma women’s presence on the fairgrounds. The oral interviews enable the researcher to move from macro level questions to the micro level, bottom-up histories of everyday life at the fairgrounds. The oral narratives provide insights into the experiences and self-perceptions of the Roma women as women, wives, mothers, and entertainers. Their gender, along with their belonging to a historically and socially marginalized ethnic community, complicates the experiences of the Roma women and girls at the fairgrounds. While the focus is on the life-histories and micro analysis, the oral accounts especially with the older women also offer insights into the transformation of the panayır culture and entertainments since the 1970s. Reading these oral accounts in tandem with the oral narratives from panayır guests, memoirs, films, and photographs, this paper sheds light on the lives of panayır women and the changing gender dynamics at the fairs.