Urban design workshops have become a quality addition to the regular education curriculum in architecture, urban design, and landscape architecture schools. In many of these institutions, short courses or workshops are introduced as an obligatory part of the design studio. However, the quality of urban design workshops varies. This study focuses on twenty-five years of experience in teaching through workshops. Workshops, which are very often an extracurricular activity, can be used as a tool for curricular renovation and flexibility because they complement the studio program. The advantages of introducing programs with urban design workshops into education is that the professional subject changes every year depending on the current events taking place in the surroundings and the profession, and, in comparison to the compulsory curriculum, this dynamic component of studying links students and practice. During the course of the workshop, the students have to focus their thoughts, work, and results in a short period. This allows them to contemplate current events, and also to assess both their individual capabilities and knowledge gained through regular studies and extending the intuitive and intellectual learning process. The main disadvantage of urban design workshops is that only by completing all phases of a workshop will participants have the best results from every perspective. The first phase of preparing a workshop, when its themes and goals are set, places a lot of responsibility on the teachers that organize the workshop. Regular work usually occupies the teaching staff, and so this phase presents a burden for their educational and other activities at the school. The second phase is the very core of the urban design workshop, when all of the planned activities come together. It is essential for the participants to share their experiences and work in a common living environment for a few days. The results of the workshop—that is, transformation of their experiences into design—are seen in the third phase thorough exhibitions, presentations, or publications. It is usually difficult to continue workshop activities after the very intensive work in the second phase. The third workshop phase requires a new investment of creative energy.