The comfort of the urban environment is one of the key factors influencing the quality of life for the population. A particular focus is placed on examining small towns (with a population of up to 50,000 people) from the perspective of their suitability for local community living. In order to comprehensively study the issue of a comfortable urban environment in the Russian provinces, the dynamics of the urban environment quality index in a number of cities in the Vologda Region were analysed, and survey materials from local residents (n = 1400) were also utilised. It is argued that sociological diagnostics complements and reveals statistical information on problem areas in urban development, allowing for the development of a unified approach to overcoming these issues, taking into account the opinions of the residents themselves. The study concluded that over the past five years, the development of small towns in the region has shown a positive trend, with an increase in the urban environment quality index being observed. However, based on the data for 2022, only 4 out of 13 small towns (Veliky Ustyug, Kharovsk, Totma, Sokol) can be considered as having a favourable urban environment. According to statistical data, the most problematic areas of the urban environment in small areas are social and recreational infrastructure and public business infrastructure. According to the opinions of residents, the quality of medical and educational services and housing availability are also significant issues. More positively, the environmental situation is evaluated in cities (as indicated by the index indicators and local residents’ judgments), as well as the level of safety and crime rates. Despite the presence of problematic areas in the development of small towns and their lag in terms of living comfort, the overall attitude of the local community toward theirplace of residence is positive, with a willingness to take responsibility for the city’s development. The results obtained serve as a basis for the policy of preserving and developing small areas, addressing social contradictions, and establishing promising directions for creating a comfortable living environment in these areas, taking into account the opinions and participation of the local community in these processes.