The essay reflects on some elements of the work of Luigi Meneghello from the point of view of the history of education. It compares them with the evolution of the pedagogical debate and with the educational experiments carried out in Italy in the first half of the twentieth century. It analyses cultural metaphors that emerge in the texts of Meneghello that recall similar images in pedagogical writings of the early twentieth century. It then examines the parallels on the subject of language: the reflections and stylistic choices made by the author that reflect the debate that characterized the pedagogy of the first decades of the twentieth century. Aspects discussed include the use of dialect, the function of language as an important element of individual and collective identity, creative writing, and cooperative writing. Meneghello’s texts are highly significant to the full and clear understanding of the evolution of pedagogical thought in relation to the social and cultural context of that period.