This research assesses the way main streets are perceived and used by pedestrians in an industrial, Central-European city—Ostrava in Czechia. The city has recently experienced shrinkage and changing patterns of socio-economic exchange, reason why this research is timely and needed in view of city center regeneration. Four main streets have been purposefully selected for this study. The research methods include questionnaires with street users (n = 297), direct observations of human activities and pedestrian counting. A link between business types and the way the street is experienced emerged. Results also indicate that vacant and unproperly managed spaces negatively affect the desire to walk on main streets. Furthermore, pedestrian volumes coupled with the amount of static activities determined several benchmark conditions for lively street segments. This research provides recommendations for policy-making and design and planning practice for regeneration of industrial city centers undergoing commercial and spatial transformation.