The article explores conflicts related to forests and parks of Estonian towns from the Middle Ages to the 1940s. A brief overview is first given of the development of urban forestry in Estonia. There are also cases where the loss of urban forests and the related problems that arose could have led to conflicts, but for certain reasons they did not emerge. The main focus of the research is on Tallinn and its nearby island of Naissaare and, to a lesser extent, on the town of Haapsalu. The cases with the probability of conflict are described on the example of Tallinn, Tartu and Pärnu. It is apparent that conflicts or preconditions for their emergence were caused by various reasons, both at the state and town level where local authorities and ownership relations played their role. But the causes of the conflicts can also be traced to the wider clash between military and political causes, economic development and the general public.