In his chapter on “Art” in Roman Britain and the English Settlements, Collingwood attempts to explain the revival of Celtic art that occurred in Britain after a period of Roman art of almost four hundred years. In his Autobiography he declared this was “a chapter which I would gladly leave as the sole memorial of my Romano-British studies, and the best example I can give to posterity of how to solve a much-debated problem in history, not by discovering fresh evidence, but by reconsidering questions of principle.” This chapter has received little attention from archaeologists and historians (and even less from philosophers), exception from Martin Henig in his book The Art of Roman Britain. I defend Collingwood from Henig’s criticisms and try to make his explanation more understandable by placing it in his own historical context. Here I follow Collingwood’s advice that we may better understand an explanation when we understand the context from which it originates. This is not to say Collingwood’s explanation is without shortcomings. I demonstrate how these are brought to light when his explanation for the revival of Celtic art is compared to more recent treatments of this phenomenon.