Later, during the 18th century, local administrative influence and power passed to the Maxwell family, descendants of Robert Maxwell, Church of Ireland Bishop of Kilmore (1643–1672), a family who later entered the peerage as Baron Farnham.

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The imprint of the medieval town can be followed in the area of Abbey Street, Bridge Street and Main Street (townlands of Tullymongan Upper and Lower).

The O'Reilly's later built a new castle in the late fourteenth century on Tullymongan Hill, overlooking the town centre.

In the 15th century, the local ruler, Bearded Owen O'Reilly, expanded the town marketplace which attracted merchants from Dublin and Drogheda.

The term "life of Reilly" was credited to the O'Reilly clans due to their great wealth and power, some of which came from their market.

They also allowed counterfeit English and Scottish coins to be minted in their territory at this time. This also entitled Cavan town to send two members to the Irish parliament.

In February 1690 it was the site of the Battle of Cavan between Williamite and Jacobite troops, during which much of the town was burned.

The Jacobite general William Nugent was killed during the battle.

, meaning "the hollow") is the county town of County Cavan in Ireland.

The town lies in Ulster, in the Republic of Ireland, near the border with Northern Ireland.

The town is on the main road – the N3 road – linking Dublin (to the south) with Enniskillen, Ballyshannon and Donegal Town (to the north). Cavan was founded by the King of Bréifne, Giolla Íosa Ruadh O’Reilly, sometime during his lordship between 1300 and his death in 1330.

During his lordship, a Franciscan friary was established close to the O’Reilly stronghold at Tullymongan and was at the centre of the settlement close to a crossing over the river and to the town’s marketplace.