The prehistoric period is well represented in Skegness by several salt working sites and scattered find spots. No evidence of permanent settlement has been recorded as of yet, however the saltern sites demonstrate that the area was actively occupied in this period. The find spots include, pottery, stone hammers and axes as well as flint tools which provide evidence of how the area was utilised in the Prehistoric period. Little is known for certain about Skegness in the Roman period; some evidence is conjectural. The coastline in the Roman period is estimated to have been 4-6km further out to sea. It is suggested that in this period Skegness was the site of a Roman fort or castle, which served as a ferry terminal between Skegness and Brancaster, in Norfolk.
The name ‘Skegness’ is first recorded in the medieval period; however, an earlier settlement called ‘Tric’ is widely believed to have been the settlement which would later become Skegness. It is suggested that the name ‘Tric’ is derived from the Latin Traiectus, meaning "Crossing" or "Ferry", supporting the theory of a Roman ferry terminal in Skegness. Further evidence is found in legal documents of the 12th and 13th centuries which record ‘Chesterland’ or ‘Casterland’ in Skegness, which is believed to relate to a Roman fort. Coastal erosion and storm damage was common along the Lincolnshire coast in the medieval period and it is believed that the Roman fort as well as the medieval town of Skegness were destroyed following coastal damage during this period. The 16th century writer and historian John Leland described the town as once being a ‘sumtyme a goeat (great) haven’ with a castle, church, and surrounding wall; however it is stated that this was ‘clene consumed and eten up with the se’. If a fort did exist in Skegness it is thought that it would have been located east of Skegness pier, although tangible evidence is yet to be recorded, and much has likely been destroyed by the sea. The origin of the name ‘Skegness’ is uncertain, it was not until the 12th century when the name appears in the record.
It is proposed that it could mean 'Skeggi's promontory' or 'beard-shaped promontory'. The elements ‘Skeg’ and ‘Ness’, Skeg may refer to the personal name ‘Skeggi’ or refer to ‘beard’, in Old Norse. ‘Ness’ is an Old Norse word for ‘a headland or promontory’. Skegness remained a small agricultural and fishing village throughout the medieval period. In the 16th century, it is widely accepted that the town of Skegness was destroyed by the sea, resulting in a new village being constructed inland. St Clement’s Church is believed to be a 15th century reconstruction of an earlier church which was destroyed at the same time as the village. Until the late 19th century Skegness remained a small village, although a hotel, The Vine, was established in the late 18th century. In the late 19th century, agricultural profits were declining which encouraged the main landowner in Skegness, the 9th Earl of Scarbrough to develop the town as a resort.
In the 1860s-70s plans were produced which laid out the streets, buildings, and parks of the later resort. Skegness was connected to the railway network in 1873, which was responsible for much of the popularity of the resort, increasing access for excursionists in the 19th and 20th centuries. It was in this period that coastal entertainments including the pier, gardens, sports areas, and promenades were established catering to the visitors, who were arriving in Skegness in increasing numbers. This was a period of rapid expansion for the town with several new hotels constructed including the Hildred and the Sea View Hotel. In the 1920s and 30s, the seafront underwent large renovations which were designed by Rowland Jenkins. These renovations included the boating lake, esplanade, bowling greens, and gardens, much of which was based upon his experiences in Europe. The town expanded to the north and south in this period with dozens of new residential areas built for the growing population of the town. In the mid 20th century, self-catering holidays overtook hotels and boarding houses in popularity and holiday parks began to be established, initiated by Billy Butlin who had begun his career in entertainment in Skegness.
Since this point holiday parks have become one of the largest industries in Skegness, catering to thousands of visitors each year. In the latter half of the 20th century more residential development also began to occur inland away from the coast, largely due to the availability of development land. Skegness is undergoing another episode of regeneration in the 21st century with the aim of improving the entertainment offer and increasing the sense of place already established within the resort town.
Skegness has a relatively varied character. The town has distinct zones which cater to different groups including tourists and the local population. HUCA 1 caters to both the local population and to tourists, with a high level of local amenities and entertainments and fish-and-chip shops. HUCA 2 is predominantly devoted to entertainment and coastal recreation with a large amount of street furniture and playful architecture. HUCA 3 was developed in the early-mid 20th century and the architecture is ornamental with a high number of guest houses and balconies. HUCA 4 was developed throughout the 20th century and is made up of residential streets, schools and a small industrial area, this character area caters to the population and is not visitor focussed. HUCA 5 has a high number of holiday parks and predominantly caters to the self-catering tourist population. Some of these holiday parks are scattered throughout the rural areas of the town away from the seafront. HUCA 6 is the predominantly agricultural area within the survey boundary, many of the field shapes reflect modern agricultural practice with many of the older post-medieval boundaries now removed. Skegness is widely known as a seaside resort and much of its architecture and design reflects this. It is also a settlement which has seen constant change, the result of maintaining its appeal to a modern audience.