The Russian Arctic is a highly urbanized region, with most towns built in the Soviet era to facilitate extraction industries as well as to provide and maintain military facilities. Global environmental and developmental changes, as well as national political decisions, open up Russia’s Arctic to massive investment and industrial and socioeconomic development. How do Russian Arctic cities, towns, and municipalities reflect on new opportunities in terms of designing their climate change adaptation strategies at a local level? Starting with theoretical discourse on urban climate change adaptation strategy, this research examines state-of-the-art challenges and trends in planning for adaptation measures in Russia’s Arctic industrial centers. Special attention is given to a comparative analysis of the cities’ climate change adaptation strategies. The role of civil society institutions and business community in the adaptation strategy planning process is explored. Moreover, conflict-sensitive approaches to ensure participatory processes for designing and implementing adaptation measures are discussed. The field component of research is based on the cities of Apatity, Arkhangelsk, Murmansk, Norilsk, Salekhard, and Severodvinsk and the towns of Monchegorsk, Nickel, and Vorkuta. The study concludes that, despite significant challenges identified, the total “balance sheet” of the Arctic cities’ efforts to enhance their adaptive capacities is very positive: Russian northern urban settlements do their best in addressing existing challenges via planning for sustainability approach. However, there is more to do, and municipalities should learn from one another’s experiences, as the different approaches can be helpful in developing adequate climate change adaptation strategies at the local level.