(St. Hilda's Abbey), and other Christian religious activities existed on the cliffs at Whitby as early as 655AD. The sky line of the cliffs and Abby dominate the Whitby area.

Between 400AD and 410AD marked the period when the Romans left Britain. In 410AD the Emperor Honorius officially informs the Britain's that they must organise their own defence.

With the exit of the Romans, Britain fell into turmoil with various warring kingdoms and invasions by the Saxons. Looting, pillaging and burning (including books) left Britain in dire straights. The Irish, who were just learning to read and write, were remote to a lot of these activities and many Irish monks (scribes) took on the task of saving and copying western literature. Although these were known as Celtic Christians , they acted as a means through which Roman and Judaeo-Christian cultures were sustained and helped in the re-introduction of these principles to Britain and the tribes of Europe.

Whitby, (St. Hilda's Abby and Saint Mary's Church) provides excellent references of Celtic/Saxon Christian activities, and thanks primarily to the writing efforts of Bede , quite a bit is known about this period. We know that Celtic Christian religious activities existed on the cliffs of Whitby as early as 655AD when King Oswy , (Northumbrian King) defeated King Penda (of Mercia), and founded monastic activities of both Men and Women. The Monastic activities flourished under the direction of Abbess Hild (Saint Hilda - a woman). The two branches of Christianity (Celtic and Roman) debated the matters that divided them the most at Whitby Abby (AD 664 The Synod of Whitby - most notably the dating of Easter), and the Synod decided in favor of Roman tradition. The Danes/Vikings began invading Northumbria around AD867, and destroyed many of the churches in the area including Whitby Abby. Later, King Edmund I took control of the area (944 AD), and moved sacred relics (including the bones of St. Hilda) from the ruins of the Whitby monastery to Glastonbury Abby.

The dark ages represented a struggle between the forces loyal to the established Druid beliefs, the Anglo-Saxon beliefs, and the new Celtic Christianity. Roman Christianity was re-introduced in the 6/7th Century, and a conflict between Christianity and paganism lasted well into 11th century. The story of King Arthur and his knights highlight this struggle. Stories such as the search of the holy grail, and the round table reflecting Christian purpose, and stories of the wizard Merlin and witches reflecting pagan beliefs. These stories not only show conflict but also cohabitation, and collaboration against common enemies. Eventually Christianity dominated through organised determination, repression, and absorbing a lot of the cultural and religious symbolism of the pagan beliefs. Almost all pagan religious sites and rituals where eventually replaced with Christian churches or symbolism.

There is not much known about the community that would have existed in and around Scarborough through this period. Evidence of Scarborough, as a distinct settlement, really did not appear until around AD966 when two vikings named Thorgil (nicknamed "Skartha meaning hare-lip) and Kormat were raiding the area and founded a settlement later to become Scarborough.