Leland stated that Maidenhead was known as Alaunodunum in Roman times. His source is unknown, and the only evidence of Roman occupation in the town are a couple of rural villas. One on Castle Hill was extensively excavated in the 19th century, but better known is that at Cox Green uncovered on the town's southern edge in the early 1960s.
In the 9th century, the Danes were said to have disembarked from their longboats at Maidenhead and fought their way through to Reading, which they subsequently made their base of operations. At this time, what is now, the centre of the town was known as South Ellington (possibly the origin Leland's Alaunodunum). It was when this little hamlet merged with the Maiden-hythe or "New Wharf", at the nearby Thames crossing that the name changed. The origins of the name are not quite that simple though. Hythe is usually accepted as Saxon for "Wharf", but there are many alternative explanations for the Maiden:
Or the whole thing could be Welsh Celtic Ma-y-Din-Heth: Place of the Fort of Barley. If the name really is modern "maidens" then these would presumably be the nuns from nearby Cookham. It is supposed that any fort or cauldron shaped remains would have stood on Castle Hill. It was originally known as Folly Hill, perhaps indicating a tree covered earthwork. Though, as seen, a Roman villa has been discovered here and its ruins were probably the folly that gave the hill its name. In the 17th century, a building called Cook's Folly did stand at the foot of the hill next to the Windsor Castle Inn (named after its view). This place was previously called the Fleece or Folly Inn and it is presumed that both pub and hill changed names around the same time. The name was the inspiration for a later castle-like folly built through a whim of Lord Desborough in 1890. It can still be seen today. Another folly in the town was Langton's Folly which stood on the site of the Magnet Leisure Centre. The ruinous facade of a Norman church, it was built by a group of tramps for a local brewer who wanted to obscure the view of his malthouse.
The chapel at the end of Moor Bridge (aka Chapel Arches) over the White Brook at Maidenhead was built without Episcopal permission on the border of Bray & Cookham parishes (near the Bear Hotel) in 1269. The town was split between these two places until it was given its own parish in 1870. The medieval chapel stood empty for fifty years until the Bishop finally allowed it to be used. The chapel became a stopping place for pilgrims who came to visit the Maiden's Head after whom, another theory says, the town was named. This was the skull of one of St. Ursula's eleven thousand virginal followers who were martyred at Cologne. Other relics of St. Ursula's followers were held at St. George's Chapel, Windsor. The young Maidenhead girl was said to have been represented on the town seal (14th c.). In fact, this is now thought to show St. John the Baptist. The town has no connection with St. Ursula who probably never existed. The chapel was rebuilt in 1726 but, a hundred years later, it was decided it was an obstruction to traffic and was torn down. A new church was built just to the north-west, but brass studs in the pavement still mark where the old chapel once stood.
Further east is Maidenhead Bridge, originally a wooden structure built in about 1280 to replace a ferry at an important crossing point of the Thames along the Saltway from Droitwich to London. It was once much longer and the parishes of Cookham, Bray and Taplow met under the central arch. There was a hermitage at the Maidenhead end and the hermit there collected offerings to maintain the crossing. After the Earl of Salisbury failed in his attempt to assassinate Henry IV at Windsor (1400) and restore Richard II to the throne, he fled first to Sonning and then Reading. His followers tried to buy him some time by holding Maidenhead Bridge. They had a pitched battle with the Royal forces for three days but were eventually overcome and the Earl was eventually captured and executed. The bridge was broken down during the Civil War to reduce the ease of troop movements. Fifty years later, in 1688, the river-crossing was almost the scene of more fighting. When the Irish soldiers of the Catholic King James II were retreating from Reading, they stopped at Maidenhead with a view to holding the bridge against the Protestant champion, William of Orange (later William III). Though they set up gun emplacements and fortified a certain brick house in the town, the Irishmen could not match William's Dutch army who sent in drummers under the cover of night to sound a retreat. In the confusion, the Catholics quickly withdrew to London. The present bridge at Maidenhead was built in stone for Sir Robert Taylor in 1772, when tolls were introduced.
It was also during the Civil War that Maidenhead had become the scene of an event of National importance. After King Charles I's capture by Parliament, he was held prisoner at Caversham Park, but was allowed a trip to Maidenhead to visit his youngest children at the Greyhound Inn. The townsfolk strew his route with flowers and Fairfax found the meeting so touching that he allowed the little Royals to return with their father. This historic inn had previously been the setting for Sir Walter Raleigh's trial for treason in 1603 because the plague of rife in London. He was sent to the Tower of London but later released. The Greyhound finally burnt down in 1735 and the NatWest Bank now stands on the site where a plaque records King Charles' visit.
Maidenhead had numerous inns and, in the 18th century, it was just about the busiest coaching stop in the country. Ninety coaches a day passed through the town. The coaching inns were, naturally, highly popular, especially at dusk when coachmen refused to carry-on over the infamous Maidenhead Thicket, for fear of being held-up by highwaymen. The demolished Sun Inn actually had an ostler who used to moonlight as one of these men-of-the-road. He would rob the coaches on the Thicket and then sympathise with the distraught occupants when they arrived at the inn! This establishment supplied extra cock-horses to pull coaches up Castle Hill. Its stables could hold up to forty horses, and the White Hart (later Woolworths) could take fifty!
Maidenhead is famous for its Railway Bridge, erected in brick on the Great Western Line by Isambard Kingdom Brunel in 1838. It has only two arches, each spanning a vast 128 ft. The right-hand one has an amazing echo and is thus known as the 'Sounding Arch'. When built, these arches were the widest and flattest in the World and an old story tells how GWR did not believe they would hold up. They therefore insisted that the wooden construction framework be left in place. However - in imitation of Sir Christopher Wren's work at nearby Windsor - Brunel lowered these temporary works so that, while appearing to support the main structure, they were actually useless. Eventually, a flood washed them away, the bridge stood alone and Brunel's true genius was revealed. The bridge is the subject of the first ever impressionist painting, JMW Turner's 'Rain, Steam and Speed' (1844).
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