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Leon O’Cathasaigh cycles through the picturesque hills of Wicklow recalling the history, tales, and legends surrounding Captain Michael Dwyer and his men. Not long ago I spent a wonderful day cycling from Rathfarnham, a suburb of Dublin City, southward into the hills and valleys of County Wicklow. The long road took me from busy streets to ancient forts and quiet valleys.

As I traveled I thought about the story of the road, known as the Military Road, and how, through the life of one man, it has come to shape Irish history and contribute to the lore of County Wicklow. The story begins far away at the other end of the road, in the Glen of Imaal in West Wicklow, and long ago, in the late 1700s when Ireland was in turmoil with the rebellion of the United Irishmen, in Wexford and elsewhere. The rebel Captain Michael Dwyer fought with General Holt at Arklow and Vinegar Hill but they were roundly defeated by the redcoats with many being captured and executed and others rebels fleeing to the hills.



With Holt’s blessing, Dwyer decided to return to his homelands in the hills of Wicklow and cause havoc by means of guerrilla warfare. This article was originally published in Ireland of the Welcomes magazine. Subscribe now! Looking into the "north prison" of Lug from Camarahill in the Glen of Imaal.

My first climb of the day was the slow drag up through Glencree to the Sally Gap. As the land rises to bleak uplands and wild bog it is easy to appreciate how inaccessible Wicklow would ha.

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