In this presentation, I explore the challenges associated with long distance women’s road cycle racing from a variety of perspectives, including athletes, managers, promoters, and governing bodies. This exploration covers several decades, c. 1950s - 1980s, from some of the earliest sanctioned international competitions to the inclusion of women’s cycling into the Olympic Games. Women in many endurance sports, including cross-country skiing and running, have faced barriers related to sex discrimination in the larger society and in maledominated sport organizations, and cycling falls into this same tradition. An analysis of both primary and secondary sources indicates that historical, biological, and socio-cultural factors have been identified as the key factors that structure the quantity and quality of long distance road cycling events for women. Primary sources include organizational records, correspondence and news clippings from the Women’s Cycle Racing Association, Women’s Challenge, Union Cycliste International and the International Olympic Committee. I conclude by juxtaposing these historical narratives about women’s cycling with my own efforts to promote the growth of women’s racing in the U.S. Sadly, many commonalities exist despite the passage of over fifty years: small women’s fields, a lack of racing opportunities, minimal mileage, questions about whether women should race with men or in women-only fields, and the difficulty of moving women from recreational to competitive riding.