This study of digger wasps (Hymenoptera: Spheciformes) was carried out in the cultural landscape of the Drwęca, Lower Vistula, and Warta river valleys in northern Poland during 2011-2013. The study was undertaken on sites representing a succession gradient from dry grasslands to high levels of tree cover which we hypothesised would influence the structure of digger wasp communities. During our research additional information on flower use, insect prey, and phenology was also recorded and is reported here, revealing dependencies between woodland cover and both the prey and nesting types of digger wasps. A total of 136 species were recorded, i.e., nearly 56% of all Spheciformes species recorded from Poland. Among the species collected, 30 were on the Red List of Threatened Animals in Poland. Most endangered species were recorded in psammophilous grasslands, which are open habitats, and the least in mesic sites. These results significantly update the known distribution of the digger wasp in northern Poland. Knowledge on the biology of digger wasps in Poland is also supplemented by information on the feeding of larvae of 14 species and information on food plants visited by imago digger wasps. The results of our research confirm the correlations between the increase in forest cover and the number of digger wasp species.