The relevance of the study consists in the new subject matter and details of geospatial support for the procedure of strategic planning in the development of regions under conditions of digital transformation. The objective of the study is to present the ideas, new views, and innovative approaches to the use of geospatial data, information, and knowledge in evaluating territorial resources and in substantiating the possibility of applying the method of geocognitive modeling to analysis of the resource potential of territories with a view to strategic planning of their social and economic development. The issues of using geospatial knowledge about a territory, of revealing and presenting territorial characteristics influencing a territory’s evaluation, balanced and efficient use of the natural resources, material, technological, human and other potentials were investigated. Findings of the study: analysis of one of the main trends in territorial development over the recent years (intensive use of geoinformation, geoinformation systems, geospatial knowledge, and geospatial analytical data in planning and management of countries and regions) was made. Formal interpretation of the evaluation and use of territorial resources as objects of a single economic system is proposed. Based on formal logical analysis, a theoretical multiple presentation of the process of analyzing the value of a territory from the viewpoint of its industrial use and spatial opportunities is made. The concept of a geo-fragment is used as an elementary unit of geospace in which industrial and/or natural processes take place and interaction of the objects of different industrial fields occurs. Theoretical and practical meaning: a new geocognitive method of evaluating various properties of a territory is proposed, including the degree of development, knowledge, and being fit for comfortable living of people and other territorial aspects. The technological interpretation of the proposed method for assessing the economic value of regional resources is provided. Conclusion: geospatial activity in the territorial context is becoming an important factor in planning territorial development when optimizing the distribution (redistribution) of territorial resources by way of complex interaction of industries and clusters. The study opens up opportunities for further development of the methods, approaches and technologies of formation and use of geospatial knowledge and geocognitive technologies.