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Watlington is about 15 miles from Oxford, Reading and High Wycombe, at the foot of the Chiltern escarpment. The Thames riverside towns of Wallingford and Henley on Thames are about 7 miles away. Junction 6 of the M40 is 2 miles to the North. The Icknield Way, an ancient route from Cromer in Norfolk to Avebury in Wiltshire, skirts the south-eastern border of the town.

Watlington's three main streets - High Street, Couching Street and Shirburn Street - form a T, with the fine 17th-century town hall at the junction of the three. Many fine buildings dating back to the 16th-century still exist today. Watlington is mentioned in the Domesday Book.
Watlington has a number of specialist shops, two schools, sports club, three pubs and many small businesses. Red Kites can often be seen soaring above the roof tops.
The Watlington area is likely to have been settled at an early date, encouraged by the proximity of the Icknield Way, an ancient and important cross country track which runs along the dry, high ground to the east. The place name means 'settlement of Waecel's people' and this indicates occupation from around the 6th. century A 9th century charter mentions eight 'manses' or major dwellings in Watlington and the Domesday survey of 1086 identifies the area as being an agricultural community valued at 610.
A church was probably built in Watlington during the Anglo-Saxon period, although one is not specifically mentioned before 1129. It is likely that early medieval settlement was concentrated around the church and as recently as 1811 it was noted that the older buildings, reputedly built entirely of wattle and daub, lay on the north side of the town. These have subsequently been demolished. The manor house, which lay to the east of the church, is first mentioned in 1250. It was owned at this time by Richard, Earl of Cornwall, as part of the honour of Wallingford, but was demolished in the early 17th century, although part of its moat is still visible. In 1252 Richard obtained a grant of market for Watlington and in 1302 a fair and second marker were instituted Although there is no documentary evidence to show that Watlington was granted a charter or was regarded as a borough in the Middle Ages, there seems to have been some attempt to lay out a planned street system, which suggests that the present settlement map have been one of the many 'planted' towns created in the 12th or 13th centuries. Certainly, the town seems to have grown away from the original settlement, leaving the church in isolation. The centre of the town is now well to the east of the church, around the fine town hall, which was built in 1665 at the expense of Thomas Stonor. This provided cover for the market and rooms above for a grammar school.

Watlington was involved in the Civil War (1642-49) and was in the middle of the fighting for many years. Royalist forces were quartered here and several skirmishes took place in and around the town in 1644 Royalist troops began fortifying the town but the king decided to move his garrison to Oxford instead, thereby preventing possible siege damage. John Hampden reputedly slept in the town prior to the battle of Chalgrove Field.

Watlington continued to grow very slowly and this has protected the historic core from redevelopment. Many medieval buildings were refronted in the 18th and early 19th centuries, often in brick or a combination of brick and flint. Watlington never benefited from the canal trade as the nearest river is six miles away. In 1822 this was described as 'a circumstance totally adverse to the prosperity of the place' and after 1852 a market ceased to be held in the town at all.

A branch railway line was built in 1859 by the Watlington and Princes Risborough Railway Company. However, this came too late to save the fortunes of the town. The fact that the line terminated at Shirburn and not Watlington may also account for the lack of prosperity brought by the railway. The line was run by the company until it was taken over by the Great Western Railway in 1884. The line was closed following the Beeching Report in 1963.

Watlington was first designated as a conservation area in 1976 with minor additions being made to the designated area in 1993