The modern town of Letterkenny began as a market town at the start of the 17th century, during the Plantation of Ulster. It may have been established on the site of an earlier Gaelic settlement. It was the first crossing point of the River Swilly. In the recent past, Letterkenny was a largely agricultural town, surrounded by extensive cattle and sheep grazing on what was then untilled hillside – at a time when Conwal (3 km west of Letterkenny) was the ecclesiastical and seaport centre. The waters of the Atlantic had not yet retreated from the basin of the Swilly, whose estuary at that time extended up almost as far as New Mills – proof of this may be found in those alluvial flat-lands between Oldtown and Port Road.
Letterkenny Chamber of Commerce and Industry was founded in 1965. It is the only Donegal Chamber of Commerce affiliated to Chambers Ireland, meaning it "provides input into national and regional lobbying policies", according to its website.
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