As the Maroons escaped from enslavement into unknown and inaccessible environments, they relied on their mental maps developed through sequential exploration of those environments to establish and defend their settlements. Initially they would take advantage of the knowledge of the areas surrounding the plantations from which they escaped, explore them thoroughly and then, at the appropriate time, link their escape routes and locations to those mental maps that they had acquired. That knowledge would have helped them to develop networks of familiar pathways and landmarks along, and around which, they arranged their settlements. This paper suggests that knowledge of such pathways and strategic locations enabled the Maroons to effectively harness the resources of the rough terrain and harsh environmental conditions to claim their freedom firstly as a forest people developing a forest-based Maroon culture, which they later transformed into a river-based culture as they moved to settle along the major waterways after the peace treaties. Examples from Suriname are used to examine the process and significance of the contribution of the geographical factor in their successes. The paper also examines the speculation that the Maroon response to the geographical factors, observed through models based on such sequential explorations and a comparative analysis of the colonial and post-colonial experience, are crucial to our understanding of the development of Maroon settlement behavior patterns, spatial arrangements and the formation of Maroon heritage.