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Kawasan di keliling Eastbourne diketahui telah ditetap di sepanjang sejarah. Pelombongan Flint dan artefak Zaman Batu lain telah ditemukan di kawasan desa yang berkelilingan, dan ada tapak Rom dalam sempadan bandar.  Pada 1717, sebuah tempat mandi Rom dan bahagian kawasan berturap telah ditemukan di antara jeti kini dan redoubt fortress di perkampungan desa yang kemudian dikenali sebagai Sea Houses, sementara pada 1841, peninggalan sebuah villa Rom telah ditemukan berhampiran dengan tempat masuk ke jeti dan terletak ditanam berhampiran dengan Queens Hotel kini. Sebuah carta Anglo-Saxon, sekitar 963 AM, menjelaskan pentas mendarat dan anak sungai di Bourne. Berikutnya Penaklukan Norman, Hundred dari apanya kini Eastbourne, telah dipegang oleh Robert, Count of Mortain, saudara seibu William yang Penakluk. Domesday Book menyenaraikan sebuah 28 ploughlands, sebuah gereja, sebuah kincir air, perikanan dan kematu garam.

Sebuah carta untuk pasar mingguan telah diizinkan ke Bartholomew de Badlesmere pada 1315–16; ini menambah kedudukannya sebagai Lord of the Manor dan memperbaikikan industri tempatan. Sewaktu Zaman Pertengahan pekan ini dilawat oleh Raja Henry I dan pada 1324 oleh Edward II. Bukti masa silam zaman pertengahan Eastbourne dapat dilihat pada Gereja St Mary abad keempatbelas dan rumah besar digelar Bourne Place.  Pada pertengahan abad keenam belas rumah itu menjadi tempat kediaman keluarga Burton, yang memperolehi banyak dari tanah yang mana bandar kini berdiri. Rumah besar ini dimiliki Dukes of Devonshire dan telah dimodelkan semula secara meluas pada zaman George awal apabila ia diganti nama Compton Place.  Ia adalah salah satu dari bangunan senarai Grade I di bandar.

Dakwaan terawal Eastbourne sebagai sebuah tempat peranginan tepi laut bermula berikutnya cuti musim panas oleh keemapt-empat anak Raja George III pada 1780 (Putera Edward dan Octavius, dan Puteri Elizabeth dan Sophia).

Pada 1793, berikutnya tinjauan pendapat pertahanan pantai di tenggara, keizinan telah diberikan untuk keposisian infantri dan meriam yang besar untuk mempertahankan teluk di antara Beachy Head dan Hastings dari serangan oleh Perancis. 14 Martello Tower telah dibina di sepanjang pesisir pantai barat Teluk Pevensey, berlanjutan sejauh Tower 73, Wish Tower di Eastbourne.  Beberapa dari menara ini terus kekal: Wish Tower adalah suatu ciri penting pinggir laut bandar, dan sebahagian dari Tower 68 membentuk tingkat bawah tanah sebuah rumah di St. Antony's Hill. Di antara 1805 dan 1807, pembinaan mengambil tempat sebuah kubu digelar Eastbourne Redoubt, yang dibina sebagai sebuah berek dan gudang simpanan, dan diawasi dengan 10 meriam.

Eastbourne tetap menjadi sebuah kawasan perkampungan kawasan luar bandar kecil hingga abad ke-19. Empat kampung atau perkampungan desa menduduki tapak bandar moden: Bourne (atau, untuk membezanya dari yang lain dengan nama sama, East Bourne), kini digelar Old Town, dan ini mengelilingi bourne (anak sungai) yang naik di Motcombe Park kini; Meads, di mana Downs bertemu pantai; South Bourne (berhampiran dewan bandar); dan perkampungan memancing hanya dikenali sebagai Sea Houses, yang terletak di timurnya jeti kini.

Pada pertengahan abad ke-19 banyak dari kawasan yang jatuh ke tangan dua pemilik tanah: John Davies Gilbert (keluarga Davies-Gilbert masih memiliki banyak dari tanah di Eastbourne dan East Dean) dan William Cavendish, Earl dari Burlington. Pemegangan keluarga Gilbert bermula pada lewat abad ketujuhbelas dan awal kelapanbelas apabila barrister Nicholas Gilbert mengahwini seorang pewaris Eversfield dan Gildredge. (Keluarga Gildredges memiliki banyak dari Eastbourne pada 1554. Keluarga Gilberts akhirnya membuat Gildredge Manor House milik mereka. Hari ini nama Gildredge terus hidup di taman bereponim.)

Pada 1752, a dissertation by Doctor Richard Russell extolled the medicinal benefits of the seaside.  His views were of considerable benefit to the south coast and, in due course, Eastbourne became known as “the Empress of Watering Places".

An early plan, for a town named Burlington, was abandoned, but on 14 May 1849 the London, Brighton and South Coast Railway arrived to scenes of great jubilation. With the arrival of the railway, the town's growth accelerated.  Cavendish, now the 7th Duke of Devonshire, hired Henry Currey in 1859 to lay out a plan for what was essentially an entire new town — a resort built "for gentlemen by gentlemen". The town grew rapidly from a population of less than 4,000 in 1851 to nearly 35,000 by 1891.  In 1883, it was incorporated as a municipal borough; a purpose-built town hall was opened in 1886.

This period of growth and elegant development continued for several decades. A royal visit by

George V and Queen Mary in March 1935 is commemorated by a plaque on chalet number 2 at Holywell.

World War II saw a change in fortunes. Initially, children were evacuated to Eastbourne on the assumption that they would be safe from German bombs, but soon they had to be evacuated again because after the fall of France in June 1940 it was anticipated that the town would lie in an invasion zone. Part of Operation Sealion, the German invasion plan, envisaged landings at Eastbourne. Many people sought safety away from the coast and shut up their houses.  Restrictions on visitors forced the closure of most hotels, and private boarding schools moved away.  Many of these empty buildings were later taken over by the services.  The Royal Navy set up an underwater weapons school, and the Royal Air Force operated radar stations at Beachy Head and on the marshes near Pevensey. Thousands of Canadian soldiers were billeted in and around Eastbourne from July 1941 to the run-up to D-Day. The town suffered badly during the war, with many Victorian and Edwardian buildings damaged or destroyed by air raids.  Indeed, by the end of the conflict it was designated by the Home Office to have been ‘the most raided town in the South East region’. The situation was especially bad between May 1942 and June 1943 with hit–and–run raids from fighter–bombers based in northern France.

In the summer of 1956 the town came to national and worldwide attention, when Dr John Bodkin Adams, a general practitioner serving the town's wealthier patients, was arrested for the murder of an elderly widow. Rumours had been circulating since 1935 regarding the frequency of his being named in patients' wills (132 times between 1946 and 1956) and the gifts he was given (including two Rolls Royces). Figures of up to 400 murders were reported in British and foreign newspapers, but after a controversial trial at the Old Bailey which gripped the nation for 17 days in March 1957, Adams was found not guilty. He was struck off for 4 years but resumed his practice in Eastbourne in 1961. According to Scotland Yard's archives, he is thought to have killed up to 163 patients in the Eastbourne area.

After the war, development continued, including the growth of Old Town up the hillside (Green Street Farm Estate) and the housing estates of Hampden Park, Willingdon Trees and Langney. During the latter half of the 20th century, there were controversies over the demolition of Pococks, a 15th century manor house on what is now the Rodmill housing estate, and the granting of planning permission for a 19-storey block at the western end of the seafront.  The latter project (South Cliff Tower) was realised in 1965 despite a storm of protest led by the newly formed Eastbourne and District Preservation Committee, which later became Eastbourne Civic Society, and was renamed The Eastbourne Society in 1999. Local conservationists also failed to prevent the construction of the glass-plated TGWU conference and holiday centre, but were successful in purchasing Polegate Windmill, thus saving it from demolition and redevelopment.

Pada 1981, sebahagian besar bandar telah digantikan dengan kedai-kedai bahagian dalam Arndale Centre. Kebanyakan dari pemanjangan megambil tempat di pinggir utara dan timur bandar, akhirnya menelan kampung-kampung keliling.  Meskipun, bahagian yang lebih kaya barat telah berada di bawah kekangan oleh Downs dan tetapi secara besarnya tidak berubah.

Pada 1990an, kedua-dua mereka berkembang dan kontroversi bertambahan secara pantas apabila pelan baru telah dilancarkan untuk membangun kawasan yang digelar Crumbles, sebuah bank shingle di pantai di timur pusat bandar. Kawasan ini, kini digelar sebagai Sovereign Harbour, mengandungi sebuah marian, kedai-kedai, dan pelbagai ribu rumah, bersama dengan flat dan pangsapuri mewah, terdahulunya rumah pada banyak tumbuh-tumbuhan jarang. Continued growth in other parts of the town, and the taming of the central marshland into farmland and nature reserves, has turned Eastbourne into the centre of a conurbation, with the appearance from above of a hollow ring. Currently under review is the demolition of some of the town centre, to extend the existing Arndale shopping centre, and the adaptation of several existing roads to form an inner ring road. In 2009 the new Towner Arts centre was opened abutting the listed Congress Theatre built in 1963.