It was the Earl of Scarborough, back in the 1870s, who was to be the leading light in the development of Skegness as a seaside resort that is still much loved by 'trippers' today. Having already brought the railway to Skegness he embarked on plans for a pier that was to become a masterstroke for the town. Skegness, unlike the majority of seaside towns, was geographically better suited to receiving passengers by sea than by rail; and the new pier would prove an instant success. The Skegness Pier Company was set up and immediately advertised a competition to design a new pier for a prize of £50. Forty-four entries were received and a design from Engineers Clarke & Pickwell provided the winner. Work commenced in 1880 and the new 1,802ft (546m) Skegness Pier opened on the 4th June the following year. Built from cast iron with a Jarrah-wood deck, Skegness Pier was the epitomy of Victorian architecture.

Approached through a rather unusual Gothic archway, almost ecclesiastical in form, and flanked by two similar Gothic kiosks, the pier opened out into a 25ft (7.5m) wide promenade. Along the uncluttered deck were ornate shelters, extending beyond the width of the neck, gas lamps spaced at regular intervals, and flagpoles completing the scene. These would by gaily dressed on bank holidays and other notable occasions. At the 'T' shaped pier-head there was a 700 seat Saloon and refreshment rooms.

The great success of Skegness Pier, as mentioned previously, was its association with the passenger steamers. Steamer trips from the pier started in 1882 and proved hugely popular. This led to a group of local businessmen starting the Skegness Steamboat Company the following year. The company's primary role was to quite simply, charter available boats for the summer season. The most popular trips were the day excursions across The Wash to Hunstanton. This passage to Hunstanton normally took between two and three hours, which left plenty of time for passengers to explore the grounds of the Prince of Wales' new estate at nearby Sandringham, before returning to Skegness by the early evening. The trip would also include a visit to the Lynwell Lightship, here passengers could explore the Lightship, whilst the crew received fresh supplies and mail. The success of these excursions soon required the pier-head to be extended with the addition of extra landing stages.

Skegness Pier provided various entertainment. The saloon was predominantly used for lectures, concerts and dances, while the pier-head itself provided regular diving displays, which were very popular at the time. Two divers, professor's Capes and Connell, were thrilling the crowds throughout much of the 1880s and 1890s. In 1898 the Saloon was extended along with the construction of new refreshment rooms.

March 1919 was to see the first major incident at Skegness Pier when the Schooner 'Europa' collided with the pier, breaching the neck. Temporary repairs were effected by August of that year, these remaining in place until 1939, when they were finally repaired as part of a restoration project. This project centred primarily on the redevelopment of the kiosks either side of the Gothic archway.

With the outbreak of the Second World War Skegness Pier was sectioned as a precaution against a German invasion, re-opening in 1948 after costly repairs. At the same time a canopy was erected at the shoreward end, being completed in 1949, and the pre-war Saloon was rebuilt. In 1971 the Gothic archway was finally replaced, along with the 1939 entrance buildings, when the shoreward end was rebuilt to make way for a new building housing, shops, cafés and amusements.

Along with most other East Coast piers, Skegness Pier was to suffer the wrath of nature in the great storm of 11th January 1978. Severe seas were to wash away two complete sections of the pier neck, leaving the pier-head and theatre isolated at sea. Various plans over the next few years to restore the structure failed due to lack of financial backing, and a decision was made in 1985 to demolish the seaward end. Dismantling of the theatre started in the October of that year, but a fire completely destroyed the building while the work was in progress. During the 1990s attention has always been focused on the shoreward end, providing an array of high-tech amusements and facilities, now such a familiar sight at Britain's popular seaside resorts.