This chapter examines how stories in the 1920s about speed-loving and adventurous female motorists and racecar drivers worked to challenge and unsettle the boundaries between masculinity and femininity. Drawing on a range of Swedish popular periodicals, from fashion magazines to motorsport journals, the investigation focuses on two (overlapping) contexts of female automobility, covering, in the first case, discourses on the cosmopolitan modern woman behind the wheel, and, in the second case, motorsports and the fate of a pioneering group of female drivers in Sweden. The analysis shows that the mobility of the driving city woman tended to be construed as modern more than masculine, whereas concerns were voiced in the press that female racecar drivers and motorcyclists would ultimately be masculinized. Though stereotyping and satire often worked to re-inscribe old gender hierarchies in motorsports, the analysis in this chapter shows that the rising overall visibility of female motorists in Sweden in the 1920s also contributed to pushing the boundaries of the cultural expectations of women’s place in the modern world—a place no longer limited to home. The modern city woman and her racing sisters claimed to be as much “at home” on the road.