I'm reading this wikipedia article and it seems like Western Christian monasticism came originally from Egypt, and then had small followings in Italy and northeastern France before somehow skipping England and going right to Scotland and Wales, and thence Ireland, where it became such a big deal that the article has a really long section about it, and there's another really long list of monasteries in Ireland. Why was Ireland so amenable to monasticism? Was it the geography? The culture? Something else?

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    It is probable that monasticism did not "skip England", which did not exist at the time, but that the Anglo-Saxon invaders obliterated Romano-Celtic culture, history and religion in the area that later became England. With the reconversion of England a few centuries later, Wikipedia also lists a large number of monasteries there too; many were founded by Normans after the Danes had destroyed large numbers of Saxon monasteries. So Ireland may have benefited from fewer pagan invaders (though Dublin suffered)
    – Henry
    Jun 1 '19 at 22:30

Paraphrasing liberally from the wiki article on Celtic Christianity, at least the following three factors played a role:

  • Because Ireland had not been part of the Roman Empire, the network of abbeys basically filled a bureaucratic vacuum. They ended up controlling large swaths of land following the growth of the monastic movement in the 6th century, and wielded great ecclesiastical and secular power.

  • Abbeys had very strong ties with the local ruling elites, in that abbots weren't necessarily ordained, and usually descended from one of the many Irish royal families. Further, the founding regulations of some abbeys specified that the abbotcy should if possible be kept within one family lineage.

  • Irish monasticism was notable for its permeability, in that people were able to move freely in and out of the monastic system at different points of life. Because of this, students would sometimes travel from faraway lands to pursue Latin scholarship in Irish monasteries. This, Ireland's isolation, and Ireland's lack of invasions during Early Middle Ages all fed into Irish monasteries becoming centers of Latin excellence.

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