This essay examines three schools in New York City—the City and Country School founded in 1914—and two founded in 1974 and 1984—Central Park East Elementary School 1 and Central Park East Secondary School—with respect to how they reflected Deweyan pedagogic practices and Dewey's belief in democratic education.1 It analyzes whether such pedagogic practices can be maintained over time. City and Country, founded by Caroline Pratt, reflected many of Dewey's ideas and remains true to its founder's vision today. CPE 1 founded by Deborah Meier with five teachers reflected the progressive ideas of its founder, many of which were consistent with Deweyan philosophy. It remains progressive although there have been recent attempts to make it more traditional. CPESS, founded by Deborah Meier, reflected both Deweyan philosophy and the ideas of Theodore Sizer. After Meier left in the 1990s, the school became less progressive and eventually was closed and then reopened as a traditional high school. These histories indicate that Dewey's work on education was at the core of all of these schools’ philosophies and practices. Although there have been uneven successes in keeping Dewey's progressive practices alive, they demonstrate that Dewey's work is relevant and is being practiced today.