Here’s a winter break message for Team Chesterfield from #oneCCPS Superintendent Merv Daugherty. Winter break for Chesterfield County students will be Dec. 19-Jan. 2; the first day back will be Jan. 3. In a change from previous years, school offices and the Career and Technical Center @ Hull will be open during winter break but will be closed Dec. 23-27 and Dec. 30-Jan. 2.