The paper discusses the evolution of regional policy in Poland from 1990 to 2010 and examines guidelines for modifying this policy in 2010-2020. Poland’s entry to the European Union in 2004 and European cohesion policy have had a substantial impact on regional policy in Poland. In recent years new important theoretical inspirations have appeared for regional policymakers, including new economic geography and the economics of location. International organizations such as the OECD, the World Bank and the EU are formulating proposals for a major modification of regional policy in the world. The research method is based on a benchmarking analysis and qualitative assessment of program documents. The results obtained by the researchers point to a shortage of theoretical foundations and the growing importance of regional policy to Poland’s socioeconomic development. Szlachta and Zaleski identify various risks connected with the implementation of a modern regional policy in Poland and formulate a set of questions about the theory of regional policymaking. In the first part of the paper, the authors discuss the experience of regional development programming in Poland since 1990. The next part focuses on the financial and institutional dilemmas of regional policymaking in Poland in the coming years. Later on the authors propose benchmarks for a National Regional Development Strategy until 2020. The paper ends with the formulation of key conclusions, recommendations and questions about the theory of regional policymaking.