Although Russia manifests some dynamics in its national policy on ageing, it still lacks comprehensive tools for the older generation wellbeing assessment both on national and regional levels. This research work is an ongoing project aimed at the development of the composite index (composite indicator) to assess the elderly population wellbeing in Russia for cross-regional comparison to equip Russian policy-makers with an essential tool and relevant reliable data to facilitate the decision-making and policy design at national, regional and local levels. The paper discusses the possibility of selecting relevant data from the pool of the official state statistics indicators to assess the elderly generation's wellbeing in 85 regions of the Russian Federation by four index domains (economic, social, health and regional environment dimensions). Due to a high geographical and territorial heterogeneity, this index can be advised to be adopted as a potential tool to monitor wellbeing across Russian regions with the focus on policy development for macro-regions. This grouping of regions can minimize transaction costs of bargaining on behalf of the 85 regions while developing national policies and strategies. The paper employs the Russian Elderly Wellbeing Index (REWI) to compare calculation results for 2014 and 2016 as well as addresses the issue of elderly population wellbeing analysis on the meso level in the context of federal districts. The authors run cluster analysis for the REWI indicators to compare clusters of Russian regions and federal districts.