Globally, many cities are aiming to encourage cycling for transportation as it integrates environmentally sustainable practices and physical activity into existing daily routines. While a large body of work examines cycling for transportation, few studies focus on one trip: cycling to the grocery store. This study sheds light on the barriers faced when cycling to the grocery store, including how some cyclists overcome them. Sixteen semi-structured interviews took place with people who cycle for transportation in Hamilton, a mid-sized city in Canada. Participants were asked to discuss their general transportation and grocery store habits, their travel modes specifically to the grocery store, and speak to what informs these travel decisions. The interviews were transcribed verbatim and coded following thematic analysis. Though all participants cycled regularly (e.g., to work or leisure), most did not regularly cycle to the grocery store. The most common barriers identified were bike parking, a lack of bike lanes, carrying capacity, and parking lots. While these barriers can exist for other cycling trips, they were often discussed as particularly pronounced for grocery store trips. Despite facing barriers, most participants did cycle to the grocery store at least some of the time. Drawing on social practice theory, this paper identifies the competences, materials, and meanings that are enacted to allow for this practice. Through understanding the various barriers to cycling to the grocery store, city planners, grocery stores, and educators can work to overcome the challenges and ultimately promote a more sustainable and healthier mode of transportation.