The present educational research is focused on the solution of didactic problem of an engineering-friendly description and explanation of the dynamics and control of Foucault pendulum-like systems, which have arisen from practical problems of boom crane dynamics in lifting-and-handling machinery and transport. An educational actuality of the present research is grounded on the absence of a proper description and explanation of this topic in available textbooks and scientific articles in the fields of classical mechanics, control engineering, transport, lifting-and-handling machinery, engineering education, mechanical engineering education, and classical mechanics education. Among learning tools this article uses the following educational techniques: Modelica-assisted simulation with acausal equation-based freeware computer system JModelica.org with Optimica extension, physical simulation techniques, allegoric fairy tale analogy, didactic transposition method and a complex of individual Modelica-enhanced students’ computational assignments. The proposed educational approach provides a broadening of students’ ideas concerning the applicability of abstract physical concepts to the theory and practice of freeware-assisted mechanical engineering education of undergraduate and graduate students majoring in dynamics and control of guided lifting-and-handling machinery. Research finding, concepts and ideas of this research have found a practical educational application through the formulation of practical computational problems of term design works, planning of MSc degree students’ works, and freeware-enhanced curriculum of Donbass State Engineering Academy, Kramatorsk, Ukraine.