Michael Dwyer was an insurgent captain in the Irish Rebellion of 1798, leading the United Irish forces in battles in Wexford and Wicklow., Following the defeat and dispersal of the rebel hosts, in July 1798 Dwyer withdrew into the Wicklow Mountains, and to his native Glen of Imaal, where he sustained a guerrilla campaign against British Crown forces.

The Irish Rebellion of 1798 was a popular insurrection against the British Crown in what was then the separate, but subordinate, Kingdom of Ireland. The main organising force was the Society of United Irishmen. First formed in Belfast by Presbyterians opposed to the landed Anglican establishment, the Society, despairing of reform, sought to secure a republic through a revolutionary union with the country's Catholic majority. The grievances of a rack-rented tenantry drove recruitment.