Seaman's Valley site was one of the few known places in Jamaica where the Maroons came into face to face combat with the colonial military in a battle that featured the largest force ever sent against the Maroons. In that encounter the colonial forces were routed in a total defeat resulting in the abandonment of arms and ammunition and personnel. This paper compares the material culture from the Seaman's Valley site and Nanny Town. This paper will then show the significance of the longstanding strategic relationship between the two locations during the Maroon struggle for freedom and even after peace negotiations were sealed by treaties in the middle of the eighteenth century. Therefore, the Seaman's Valley site is depicted not only as a unique battleground, with a strategic and spatial relationship with Nanny Town in the Blue Mountains. It also, was a special brewing ground for the formation and transformation of Maroon material culture in eastern Jamaica.