This article examines the history of Canada Olympic Park (COP) as it transitioned from the Paskapoo Slopes to a venue for the Calgary 1988 Winter Olympic Games and how the site framed the fight for gender equality in the sport by women ski jumpers in Canada. Ski jumping is a sport that can be considered a “nature sport” as it is practiced in the open air while simultaneously relying on built environments. Understanding the COP ski jumping venue as a “sportscape” and a gendered landscape provides a unique opportunity to explore the tensions between land, air, and the body in this nature sport. Historical analysis of the XV Winter Olympic Games inventories held at the City of Calgary Archives is combined with autoethnographic reflections of my past experiences as a ski jumping athlete who trained at the COP ski jumping venue and plaintiff in the court case to get a women’s ski jumping event added to the 2010 Winter Olympic Games to frame my analysis. This paper argues that women ski jumpers at COP carved out spaces of resistance for themselves, shifted the gendered landscape of the ski jumps, and effected change across generations of women ski jumpers on and off the hill.