Incorporated into the parish system under the tutelage of the Church Missionary Society (CMS), Waterloo was settled by soldiers from the second and fourth West India Regiment from Jamaica and Barbados.

The settlers were later joined by several groups of Recaptives, whose integration into the village community was facilitated by Governor MacCarthy's insistence on education and religion via schools, personages and churches.

With the inculcation of Christian values and Western education, and under the supervision of the village headman (who enforced the rule of law), Waterloo evolved as a stable economic, cultural, and socio-political centre.

Throughout the 19th and 20th Centuries, the city continued to serve as a gateway to and from the hinterland and blossomed as a trading centre into which goods and services from Freetown and the Sierra Leone peninsula converged.

The prosperity which reigned in Waterloo throughout the 19th and 20th centuries was shattered by the outbreak of the Sierra Leone Civil War in the 1990s, during which rebel soldiers pillaged and ravaged homes, schools, churches, offices, and government buildings, with many inhabitants fleeing the town.

Intermarriages between the newly arrived ex-servicemen from Barbados and Jamaica and the Africans liberated from slavery generously enriched elements of culture in the town.

In addition, the skills, knowledge and attitudes that the new settlers acquired facilitated their integration into the new settlement and provided the foundation for cultural adaptation and socio-economic reconstruction.