To share the experiences of stakeholders in a school district's response to the COVID-19 pandemic, especially related to supporting the district in the reopening process and sharing key decision points, challenges, facilitators, and overall lessons learned that may be applied to future emergencies. A descriptive study of participants' experience that included (1) a content analysis of policy documents and recommendations that were developed and published by key stakeholders and (2) interviews with stakeholders in the school system that were coded to identify patterns and themes. Remote interviews conducted over Zoom. Participants live or work in Brookline, Massachusetts. Fifteen qualitative interviews were conducted with school committee members, principals, members of school leadership, school nurses, school staff, parents, advisory panel members, and physicians collaborating with the school district. Whether patterns and themes related to challenges, solutions, and recommendations for future management of public health emergencies in the district could be identified. Challenges experienced during a school district's response included staffing burdens, changing scopes of services, the difficulty of successfully enforcing social distancing, addressing staff and family fears, meeting informational needs, and limited resources. Multiple interviewees shared that they felt there should have been a greater emphasis on mental health in the district's response. Successes of the response included the creation and implementation of a consistent communications system, recruiting volunteers and mobilizing the community to address critical needs, and effective technology expansion and usage in schools. Leadership and community collaboration were essential to the response to the COVID-19 pandemic in addition to strategies used to enhance coordination and communication and relay information across the community.