Nicholas Pynnar’s survey of 1618/19 provides a snapshot of this fledgling settlement, noting that thirty houses had been built near Sir John Kingsmill’s fortified residence, or bawn, all occupied by English families. This deliberate colonisation effort aimed to establish a loyal Protestant presence in the region, fundamentally altering the social and cultural landscape of this part of Ulster.

Sir John Kingsmill’s influence over Castlefinn grew considerably when, in 1631, he was regranted the lands and the settlement was elevated to manor status. With this came important commercial privileges; the right to hold a weekly market every Monday and two annual fairs. The first fair ran for two days following the feast of Pentecost, whilst the second coincided with St Martin’s Day on 11 November, lasting two days as well. These regular gatherings would have transformed Castlefinn into a vital economic hub for the surrounding countryside, drawing traders, farmers, and merchants from across the region.

By 1836, when the Ordnance Survey Memoirs were compiled, Castlefinn had evolved into a substantial town of approximately 700 inhabitants, complete with a market house that had stood for over two centuries. The memoirs paint a vivid picture of a bustling settlement where whiskey shops significantly outnumbered other retail establishments; a detail that speaks volumes about local priorities. The town maintained its Monday market tradition and had gained additional importance as a postal hub, with daily mail coaches passing through en route between Londonderry and Sligo. Today’s Castlefinn still occupies the same ground as Kingsmill’s 17th century plantation village, its streets following patterns laid down four centuries ago.