On-farm assessments play an important role in evaluating animal welfare at the farm level, ensuring legislative standards are being met and providing farm owners with information. With the recent revision of the Canadian National Farm Animal Care Council's (NFACC's) Equine Code of Practice, determining how well these standards are met in the Canadian industry is a major step in evaluating the welfare of horses within the industry. To that end, an on-farm welfare assessment tool designed to evaluate farms to the NFACC's Equine Code of Practice was designed and tested on a diverse group of volunteer farms in Southern Ontario (n = 26). This pilot on-farm welfare assessment tool was completed, on average, within 144 ± 15 minutes, and the duration was affected by the total number of horses on-farm, the number stalled at night, and the order in which the assessments were conducted. In addition, the information gathered from these assessments demonstrated not only the diversity between farms but also within farms, and this lack of uniformity in their care added additional challenges to on-farm assessment procedures. Interviews with participants and assessors helped to identify areas in which a welfare assessment program would be useful to the Canadian industry as well as areas where implementing such a program would prove challenging. This project laid the groundwork for future studies regarding the implementation of an on-farm welfare assessment tool, demonstrating that despite the lack of legislative pressure, on-farm welfare assessments have the potential to help improve the welfare of animals in the Canadian equine industry.