[2][3] In 1608, with a party of just 33 retainers from Scotland,[4] Ochiltree erected a strong bawn of limestone overlooking Lough Roughan (converted by his son Andrew Steuart into a castle) and laid the foundation of a village.

[2] Following Ochiltree's death in 1629, Roughan Castle and estate passed in succession to Robert Stewart of Irry, a cousin related through both his mother and his (first) wife to the Irish O'Neills.

[5] During the 1641 Rising he was appointed to a rebel command under Sir Felim O'Neill of Kinard but in the unfolding War of the Three Kingdoms switched alliances taking a commission from Charles II.

[6] As had the great Hugh O'Neill after the Nine Years War (en route in 1607 in what became known as the Flight of the Earls), at the end of the Cromwellian reconquest of Ireland[7] in 1653 Felim O’Neill took shelter on an old crannog in Lough Roughan.

[10] In 1784, during the American War of Independence, the Irish Volunteer supported (Masonic) Yankee Club of Stewartstown voted an address to George Washington composed by the Presbyterian minister Thomas Ledlie Birch.

It expressed their joy that the Americans had succeeded in throwing off "the yoke of slavery" and suggested that their exertions had "shed a benign light on the distressed Kingdom of Ireland".

[11][12] While patriotic sentiment in favour reform surged again following news of revolution in France, the only action associated with the United Irish insurrection of 1798 witnessed in Stewartstown occurred the previous July.

Largely Anglican and Orange Order local yeomanry (joined in the heat of the battle by English and Scottish Fencibles), attacked members of the Kerry Militia, Catholic conscripts whom the government had sought to billet in the village.

In 1837, Samuel Lewis's Topographical Dictionary of Ireland described Stewartstown as "a highly respectable and flourishing little market-town":The town consists of a spacious square and three principal streets, well-arranged, and the houses well-built of stone and roofed with slate - many of the habitations are large and handsome, several of modern erection, and the whole place has an appearance of cheerfulness and prosperity.

The town at one time carried on an extensive trade in the manufacture of linen and union cloth, and there is still business done of some consideration in this branch; and likewise in lime, quarried in the neighbourhood.