Holycross, on the River Suir in County Tipperary, takes its name directly from a relic of the True Cross that was kept at its Cistercian abbey, and that single object shaped the settlement's entire trajectory for centuries. Pilgrims came, a fair green grew up at the western edge of the village, and a stone bridge was built across the Suir to handle the traffic. Part of that fair green survives still.

The Cistercians founded their monastery here in 1180, and by 1185 to 1186 Domhnall Ua Briain, King of Limerick and the abbey's founder, had granted it a formal charter. The Cistercians were a reform movement within Benedictine monasticism, favouring austerity and rural settings, and Holycross with its undulating countryside along the Suir suited their requirements well. The charter was subsequently confirmed by Prince John as Earl of Morton, and further royal confirmations came under Henry III and Richard II, giving the community a long thread of royal backing. The abbey's status shifted substantially in 1539 to 1540, when it was converted into a secular college, a common fate for monastic houses during the Tudor reformations. That college lasted only until 1561, after which the property passed to the Earl of Ormonde, though the building continued as a parish church and a centre for pilgrims, which says something about how deeply embedded the relic's reputation had become. In 1580, the abbey, town, and all associated income were granted to Philip O'Keane and Thomas Archer. By 1563, the Dissolution of the Monasteries referred to it plainly as the "town of Holycross", indicating that a functioning urban settlement had coalesced around the religious site.

By the later seventeenth century the place was still lively enough to support two annual fairs, recorded in 1667, and in 1626 a licence was issued to Edward Boyton and his son to keep a tavern or wine cellar in their mansion house at Holycross, which suggests a community with enough passing custom to make such an enterprise viable. The medieval stone bridge immediately north of the abbey complex, rebuilt in that same year of 1626, and the Abbey Well, a holy well located roughly ten metres north-east of the church, are both physical remnants of a place that was, for several centuries, genuinely significant on the map of Irish religious and commercial life.