The earliest plans for a railway for Tenterden were made in the 1850s. The South Eastern Railway proposed that their Ashford to Hastings line should pass through Tenterden but a more southerly route through Appledore and Rye was chosen in 1851, largely through military influence. In 1855, 1864, 1872, 1876, 1882 and 1895 plans to build a line to Tenterden from either Headcorn or Paddock Wood were proposed but all failed to materialise.

In 1896, new proposals were put forward to construct a railway from Robertsbridge on the Tonbridge-Hastings line to Tenterden. These were authorised and Holman Fred Stephens was appointed to engineer the line as a light railway. The Rother Valley Railway, as it was initially known, was the first line to be built under new legislation that encouraged the building of such cheaply constructed lines in remote rural areas. The constructional standards adopted were those recommended by theorists of the construction of light railways. Such cheap construction was known to have a limited life but reconstruction from profits was thought possible. The first section of the Rother Valley was opened on 2 April 1900 to a station at Tenterden, in fact that station now known as Rolvenden. Initial success caused the directors to obtain powers for, and plan extensions to, Cranbrook, Appledore, Pevensey and Rye. None of these was built but an extension up the hill to the present Tenterden Town Station was opened in 1903 and an extension to Headcorn was opened in 1905. A further extension to Maidstone was authorised but funds were not forthcoming to complete this.

The now renamed Kent & East Sussex Railway enjoyed a modest prosperity, albeit with a subsidy for its northern extension from its neighbouring South Eastern & Chatham Railway, but sank into increased losses and bankruptcy in 1931. Unlike most railways it had not lost its independence in the four great companies created by the government in 1923 and Colonel Stephens, as he now was, had to use great ingenuity to maintain some sort of financial balance during the 1920s. He introduced a new form of train in 1923 with two Ford road buses linked back-to-back and fitted with metal rail wheels. This was financially successful but not particularly popular with passengers who were, by this time, deserting for the more convenient road buses. Nevertheless the railway continued to provide an essential service for the rural community, particularly for farmers, that it was designed to serve. Good management after Colonel Stephens death in 1931 by his successor, W H Austen, ensured survival through the 1930s and the Second World War until the railway finally lost its independence when all the railways were nationalised in 1948.

Nationalisation brought many material benefits to the railway as improvements were made, but traffic was ebbing away to the roads. During a typical week in 1953 only 118 passengers travelled on 90 trains, many of which ran empty. The inevitable result was that the line was closed to passengers on 2 January 1954 and the Tenterden to Headcorn section lost all traffic and was pulled up. Goods continued to be hauled on the original section and the occasional passenger train, particularly for hop-pickers and ramblers, appeared in the summer. By 1961, however, nearly all traffic had gone and the railway was closed.

During the period of the railway's independence and insolvency in the 1920s and 1930s, railway enthusiasts and others had become attracted to the railway's eccentricities and uniqueness. In 1948 the magazine Punch was sufficiently moved by the loss of independence to commission a poem illustrated by the eminent cartoonist, Roland Emmett, called The Farmers' Train. Such sentiment showed how the railway had become a local, indeed a national, institution and soon after closure a society was formed with the object of preserving the line. The founders had a 13 years struggle ahead of them before the first trains were run. Protracted legal battles with the then Minister of Transport saved the line from demolition but the line was only saved when the society agreed to drop the Bodiam-Robertsbridge section with 3 road crossings from its restoration plans. Negotiations then proceeded quickly and the present registered charity took over the line in 1973. Years of neglect and the original lightly engineered nature of the railway meant that the task had to be tackled in stages. The first 2 miles at Tenterden were opened on 3 February 1974. A major renewal of a river bridge enabled an extension by 1977 to Wittersham Road. Further consolidation was then necessary but Northiam was finally reached in 1990 and Bodiam in the year 2000, one hundred years after it first opened.