The area known as The Deepings has a long history of habitation going back to prehistoric times.  The land is low lying and in the distant past it was frequently covered by the sea as waters rose and receded with each ice age. Through this land flows the River Welland which in ancient times was a tributary of the Rhine when Britain was physically joined to the continent of Europe.

It is a land upon which roamed such animals as the mammoth elephant and woolly rhinoceros. From time to time modern day gravel diggings reveal the remains of these wondrous creatures and farmers, with their deep ploughs still to this day, uncover huge logs of bog oak, birch, pine and yew. These finds of  buried logs have been so numerous in the past that some farmers in the late 19th century reputedly used the ancient timbers to erect fences. It is sad to say that all the surrounding forests have long ago been cleared and the lakes drained to be replaced by a flat monotonous prairie land, dissected by straight drain channels and punctuated by the occasional tree. Only where the gravel diggings have been worked out and nature allowed to run riot have lakes returned and woods grown to give an insight of lost habitat.

The area is also rich in archaeological sites covering all periods from Neolithic to Bronze, Iron, Roman, Saxon and Norman. At one time the land adjacent to the Deepings was a huge swamp with occasional spots of high forested ground inhabited by Celtic peoples who navigated around the swamp in small skin covered coracles and lived from fishing and hunting. 

It was the Romans who first started the long and difficult process of draining the area when they constructed the Car Dyke, which even by modern day standards was an extraordinary feat of engineering. The canal had two roles, firstly as a catchwater drain, diverting the east flowing waters away from the fens and secondly as a water highway used to carry goods and trade. It was no small affair either, with a width of around 60 feet and a length of more than 122km, it must have taken years to construct and yet for a monument almost comparable in length to Hadrian's Wall, there is little information available about the Car Dyke or its builders. The canal started at Waterbeach in Cambridgeshire, then crossed the River Welland at Deeping St James (next to where today's Market Deeping Antiques and Craft Centre is located) and headed North (in line with Godsey Lane). The canal continued in a Northerly direction skirting the western limits of the Fenlands and joined the River Witham a few miles below Lincoln.

Long after the Romans had departed, the difficult process of draining the surrounding fen land continued with varying degrees of effort (and success) for centuries and was not completed until the 18th century. Even in relatively modern times, the Deepings have been subjected to widespread flooding, the last being in 1947.

It was the Saxons to whom we owe the name Deeping.  The suffix -ing or -inghes, was generally added by Saxons to a person's name and means - the land, meadows or place of that person.  In the case of Deeping,  the name probably derived from the nature of the land itself. Some suggest the name is a derivation of "deep in fen" whilst others maintain that in Saxon times the word meant deep (Old English diope) or low lying lands (-ings). 

A vellum roll now held in the British museum contains a series of drawings illustrating the life of StGuthlac who became a Hermit on the island of Crowland in the Lincolnshire marshes in AD699.  Guthlac was a Saxon nobleman who in his youth served in the armies of King Ethelred of Mercia but at the age of 24 Guthlac resolved to dedicate the rest of his life in the service of the King of Kings and became a Hermit. Guthlac is believed to have journeyed from the monastery of Repton with one companion along the Roman King Street to West Deeping.  Having proceeded by road to what became known as Deeping St Guthlac (now Market Deeping) he consulted a boatman called Tatwin who agreed to row the two friends along the Welland to a remote island (Crowland) in the fens where they arrived on St Bartholomew's day. 

Records show that in 1048, Egelric the Bishop of Durham, having collected sufficient money, had constructed an all weather road through the dense forests and deep marshes of Deeping as far as Spalding.

1066 and all that brought the Normans who encountered local Saxon resistance in the form of Hereward the Wake. Although Hereward the Wake was eventually defeated by the Norman invaders, the Wake family name keeps appearing in the history of the Deepings and the surrounding area.

The Deepings are mentioned in King William's  Doomsday Book where they are chronicled as East (Est Depinge) and West Deeping. East Deeping comprised of the two parishes of St James and St Guthlac.

In 1220 Henry III granted William Briwer, who was related to the Wake family, the right to hold a Market in the "manor of Deppinge".  In 1300 Edward I granted Baron John Wake the charter of the market of Deeping.  However, John died shortly afterwards and in 1304 his widow Joan Wake was granted the charter

"that she shall have for the term of her life a weekly market on Wednesday at her manor of East Deeping, County Lincoln ad a yearly fair there on the vigil and feast of St Michael and the six days following" 

In 1308 Edward II renewed the charter in perpetuity to Joan and her son Thomas Wake and their heirs. 

Thomas Wake went on to marry Blanche daughter of Henry Plantagenet. Thomas died in 1349 leaving no issue (Blanche lived on until 1357).  Upon the death of Thomas Wake his estate passed to his sister, Margaret, widow of Edmund Earl of Kent (beheaded 1330). Margaret only survived Thomas by a few months and on her death in September 1349 the estate and barony passed to her surviving son, John Earl of Kent. On his death in 1352 the estate passed to his sister and ultimate heiress, Joan Plantagenet (Joan The Fair Maid of Kent) who became the Countess of Kent & Lady Wake of Liddell. In 1360 Joan, whose beauty was renowned,  married the Black Prince.  By this marriage, the manor of Deeping passed to the crown and remained a royal manor until sold in the 19th century. Although Joan did not become Queen she was the first Princess of Wales and she was also mother of  Richard II.