The destruction and massacre meant that very little remained to be recorded in the Domesday survey of 1085. Scarborough recovered under King Henry II, who built a stone castle on the headland, and granted charters in 1155 and 1163, permitting a market on the sands, and establishing rule by burgesses.
Edward II gave Scarborough Castle to his favourite, Piers Gaveston. In his castle at Scarborough, Gaveston was besieged by the barons, captured and carried to Oxford for execution.
In the Middle Ages, Scarborough Fair, permitted in a royal charter of 1253, held a six-week trading festival attracting merchants from all over Europe. It ran from Assumption Day, 15 August, until Michaelmas Day, 29 September. The fair continued to be held for 500 years, from the 13th century to the 18th century, and is commemorated in the song Scarborough Fair:
Are you going to Scarborough Fair?
—parsley, sage, rosemary and thyme....
Scarborough and its castle changed hands seven times between Royalists and Parliamentarians during the English Civil War of the 1640s, enduring two lengthy and violent sieges. Following the civil war, much of the town lay in ruins.
In 1626, Elizabeth Farrow discovered a stream of acidic water running from one of the cliffs to the south of the town. This gave birth to Scarborough Spa, and Dr Wittie's book about the spa waters published in 1660 attracted a flood of visitors to the town. Scarborough Spa became Britain's first seaside resort, though the first rolling bathing machines were not noted on the sands until 1735. The coming of the Scarborough–York railway in 1845 increased the tide of visitors. To this day Scarborough railway station holds the record for the longest seat in any railway station in the world.
This influx of visitors convinced a young architect (John Gibson) with an eye to the future to open Scarborough's first purpose-built hotel. In
When the Grand Hotel was completed in 1867 it was one of the largest hotels in the world and one of the first giant purpose-built hotels in Europe. Four towers represent the seasons, 12 floors represent the months, 52 chimneys represent the weeks and originally 365 bedrooms represented the days of the year. A blue plaque outside marks where the novelist Anne Brontë died in 1849.
During World War I, the town was bombarded by German warships of the High Seas Fleet, an act which shocked the British (see Raid on Scarborough, Hartlepool and Whitby).
In June 1993 Scarborough made headlines around the world when a landslip caused part of the Holbeck Hall Hotel, along with its gardens, to fall into the sea. Although the slip was shored up with rocks and the land has long since grassed over, evidence of the cliff's collapse remains clearly visible from The Esplanade, near Shuttleworth Gardens.
Scarborough is one of Yorkshire's 'renaissance towns', having been granted government support for securing a vibrant future. As a result there are many building projects to renovate classic Victorian buildings and quality contemporary architecture
Inhabitants of the town are generally referred to as Scarborians. Natives of Whitby, call people from Scarborough, Algerinos, the origin of this nickname comes from the sinking of a boat called 'The Algerino' not far from Scarborough. The lifeboat crews of several neighbouring towns, (Whitby, Robin Hood's Bay, etc.), responded while the Scarborough lifeboat did not, and so as a constant reminder they are referred to as 'Algerinos' and Scarborough 'Algerinoland'.