Background: Top public health experts and organizations strongly recommend universal masking for children older than 2 years old during the COVID-19 pandemic, but speculate it may be difficult for young children. This study sought to assess the usage of cloth face masks in grades pre-K-2 and identify associated characteristics and adverse events. It is the first data to assess mask wearing by young children in school. Methods: This online, prospective, observational, survey in multiple schools within a single school district in a major metropolitan area measured adherence to face covering mandates by students in grades pre-K-2 as measured by percentage of day with appropriate face mask wearing per report via daily teacher surveys for the first 4 weeks of school. Results: The primary outcome was percent of the day that the entire class was wearing their masks appropriately. Of the estimated almost 1000 students and 1048 classroom days reported, the mean percentage of the school day with appropriate mask usage was 76.9%. Conclusions: For a majority of the day while conducting in-person instruction, children in grades pre-K-2 are able to adhere to mask wearing as a key mitigation strategy for limiting SARS-CoV2 infection spread and possible future use.