Although there were people prior to the first settlement, The first real settlement was soon after the Abbey was founded in 969 AD. The Abbey was founded by Duke Ailwyn (hence, Ramsey Ailwyn Community School) as a gesture of gratitude for being cured of a fever after he had a vision in his sleep.

Although a few people already lived in Ramsey it was only with the establishment of the Abbey that a real community started to form. The local community was reliant upon the inhabitants of the Abbey and the visiting pilgrims and so as the wealth and power of the Abbey grew, so did Ramsey. By the 13th Century it had become a fully functional town with a fair and Wednesday market.

The Distance in which the Abbey ruled could have been anywhere between one to three miles so as you can imagine, Ramsey was always in its power. The Abbey ruled Ramsey and built a court-of-law, a prison and a set of gallows. The Abbot of the Abbey had the power to use this equipment to enforce his own laws, put people in prison who didn't abide by them and execute the criminals.