When the COVID-19 pandemic was declared in March 2020, the lives of families all over the world were disrupted. Many adults found themselves working from home while their children were unable to go to school. To better understand the potential impact of these educational disruptions, it is important to establish what learning looked like during the first school shutdown in the spring of 2020, particularly for the youngest learners who may feel the longest lasting impacts from this pandemic. Therefore, the purpose of the current descriptive study was to gather information on how kindergarten teaching and learning occurred during this time, what the biggest barriers were, and what concerns educators had regarding returning in person to the classroom setting. The sample for the current study was 2569 kindergarten educators (97.6% female; 74.2% teachers, 25.8% early childhood educators) in Ontario, Canada. Participants completed a questionnaire consisting of both quantitative scales and qualitative open-ended questions. Educators reported that parents most often contacted them regarding technological issues or how to effectively support their child. The largest barrier to learning was the ability of both parents and educators to balance work, home life, and online learning/teaching. With regards to returning to school, educators were most concerned about the lack of ability of kindergarten aged children to do tasks independently and to follow safety protocols. Our findings highlight unique challenges associated with teaching kindergarten during the pandemic, contributing to our understanding of the learning that occurred in Ontario during the first COVID-19 shutdown.