Isolated fragments of semi-natural habitats are often embedded in a landscape matrix that is hostile to organisms of conservation concern. Such habitat islands are prone to changes in their biota over time. For insects, few studies on long-term trends in species richness within conservation areas are available, mainly due to the lack of historical data. We here use moths in the coastal pine wood reserve Pineta san Vitale (Ravenna, NE Italy) to assess how local fauna has changed over the last 85 years. This reserve has experienced massive changes in vegetation structure due to secondary succession. We compared historical collections (1933–1976: 107 species; and 1977–1996: 157 species) with our own samples (1997–2002: 174 species; and 2011+2012: 187 species). Over the last 85 years, the proportion of habitat generalists in relation to all recorded moth species increased from 20 to 33%. The fractions of woodland and open habitat species concomitantly decreased by 10 percentage points, respectively. Amongst woodland and habitat generalist species, gains outnumbered losses. In contrast, 18 species of open habitats and 10 reed species were lost over the decades. We attribute these changes to vegetation succession and to the isolation of the reserve. Generalist species are presumably better able to pass through anthropogenically exploited landscapes and colonise isolated habitat fragments than habitat specialists.