What they are walking over, in many cases, is a medieval borough that effectively disappeared from the landscape twice: once when it burned in 1376, and again when the earls of Dunraven replanned the village in the nineteenth century, absorbing portions of the old town into the walls of their manor demesne. The result is an unusual historical puzzle in which the monuments survive, including a castle, an Augustinian friary, a Trinitarian abbey, and a Franciscan friary, but the town that once connected them has had to be painstakingly reconstructed from documents, aerial imagery, and the soil itself.

The placename derives from the Irish Ath Dara, meaning the ford of the oaks, and there is no evidence of settlement here before the Anglo-Normans arrived. By the thirteenth century, however, Adare was substantial enough to be granted the right to hold a fair in 1226, and by 1310 it had received a grant of murage, that is, the right to collect tolls for the upkeep of town walls, indicating it held recognised borough status. Those walls have left no visible trace above ground, and it is thought they may have been earthen ramparts with timber palisades rather than stone. The town was attacked and burned in 1376, and its decline appears to have followed from that event. A crucial document for understanding what came before the Dunraven replanning is the 1656 Down Survey parish map of Ballingaddy, held in the National Library of Ireland, which shows the layout of burgage plots, the long narrow strips of land allocated to town tenants, laid out in rows either side of what is now the N21. A lidar survey published by Transport Infrastructure Ireland in 2018, using data collected in 2010 and 2011, revealed that the pattern of those plots is still faintly legible in the landscape, and that a pair of parallel features at the eastern end of the settlement points strongly to the line of a defensive bank and ditch running toward the River Maigue.

Archaeologist Avril Purcell excavated part of one of those burgage plots between May and August 2017, during groundworks at the Adare Manor Hotel and Golf Resort, and recovered over 5,000 finds, the majority medieval in date. These included locally made ceramics, imported Saintonge ware from south-west France, iron nails and knife blades, copper alloy finger rings and a buckle, lead weights, animal bone, and spindle whorls used in spinning thread. No definitive structural remains came to light, but the density of material suggests a busy domestic occupation that may have lasted only a few generations before the town's fortunes turned. The visible medieval remains, the friary ruins in particular, are accessible and well signed; the invisible town beneath the golf course and the demesne parkland is another matter, best appreciated through the Down Survey map and the lidar imagery, both of which are available online and repay careful attention.