This  study aimed to test the feasibility of implementing and evaluating a healthier checkout pilot study in a convenience store chain in New Hampshire. A quasi-experimental study was conducted comparing a 3-month ‘healthier checkouts’ intervention in ten convenience stores which stocked eight healthier items in the checkout space and ten comparison stores assigned to continue stocking their current checkout space product mix. All aspects of the intervention were implemented by the retailer. The research team conducted in-person fidelity checks to assess implementation. Sales data were collected from the retailer in order to compare mean baseline to intervention sales of the eight healthier items in intervention and comparison groups while controlling for overall store sales. The increases in sales of healthier items between the baseline and intervention periods among the intervention and comparison stores were not statistically significant; however, the overall pattern of the results showed promising changes that should be expanded on in future studies. Intervention fidelity checks indicated that results may have been attenuated by variability in intervention implementation. This study advances the evidence for effective promotion of healthier food purchases in the convenience store chain setting and adds to the current literature on retail checkout space interventions. Additional research is needed to confirm and expand these results.