The genus Quercus, including species like pedunculate oak (Quercus robur L.), can play a key role in maintaining climate-resistant mixed forests due to its broad ecological spectrum and drought tolerance. Unfortunately, in some parts of Europe, clearcutting has drastically reduced the oak population. An example of this event is our survey of heritage Oak—Lime forests in European Russia, which were transformed into pure aspen stands. The aim of our study was to provide forecasts and silvicultural recommendations for the passive restoration of these forests. We took a chronosequence approach to assess changes associated with natural succession over 60 years. In our survey of the development of oaks, limes and accompanying tree species (aspen, birches, maples, elms), we used 190 plots ranging across a wide spectrum of forest disturbance due to clearcutting. We demonstrate that aspen reproduce rapidly by root suckers after cutting and occupy more than 60% of the space. But the dominance of aspen decreases continuously from the age of 30, and then the lime trees begin to dominate. Oak does not show successful natural regeneration. Therefore, we recommend planting oak seedlings or sowing acorns, i.e., active restoration, in combination with the natural restoration of lime.