The town was founded around 966 AD as Skarðaborg by Thorgils Skarthi, a Viking raider, but in the 4th century there was a Roman signal station on what is now the Castle Headland, and there is evidence of much earlier Stone Age and Bronze Age settlements.
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, the 29th September. The fair continued to be held for 500 years, from the 11th century to the 18th century, and is commemorated in the song Scarborough Fair.
In 1626, Elizabeth Farrow discovered a stream of acidic water running down the cliff and into the sea in the South Bay. The water healed ailments because of it's chemical make-up, much like stomach salts in chemists do today. A Dr Wittie book about the spa waters published in 1660 was a huge catalyst for visitors to 'Scarborough Spa' and the town became Britain's first seaside resort.
The famous old bathing machines didn't make an appearance until 1735.
In 1845, the Scarborough to York railway line opened, leading to a boom in the size and population of the town, with many of Scarborough's great landmarks being built, such as The Grand Hotel which when opened in 1867 was the largest hotel in Europe! Four towers represent the seasons, 12 floors represent the months, 52 chimneys represent the weeks and the original 365 bedrooms represented the days of the year.
During World War I, Scarborough was bombarded by German Warships which also attacked Whitby & Hartlepool. The day marked the first death on British soil of the Great War and shocked the country.