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Maidenhead is twinned with its near neighbour, Windsor, in a double borough. It grew up as the home of the elite whose homes still spread out along the Thames. At the top of the social pyramid were the Astors who lived at Cliveden House, an 18th century palatial mansion in the most amazing setting overlooking the river from the Buckinghamshire side of the Thames. It now belongs to the National Trust who open the grounds and a small number of rooms to the public throughout the Spring and Summer. However, it is mostly taken up by the most exclusive hotel in the country. It was the scene of the infamous events of the Profumo Affair of the 1960s.

As an 18th century town that grew up on the border of the villages of Bray and Cookham, there are few old buildings in Maidenhead. Though there are some interesting pubs, like the Bear Hotel, which used to serve the vast coaching industry along the Bath Road. Maidenhead was a particularly popular stopping point travelling west, as the nearby 'Thicket' was notorious for highwaymen and coachmen did not like to cross it at night. Today this once infamous common has been much reduced in size, but it is still a pleasant place for a stroll. There are the remains of an Iron-Age enclosure to examine, laid out by the National Trust. It may have been a farmstead or even a temple. Nearby the old Shire Horse Centre has now closed and you can no longer see the mighty horses that once pulled the brewers' drays.

Maidenhead boasts the standard range of High Street shops in a compact shopping area. The NatWest Bank is notable as the site of the Greyhound Inn where King Charles I met his children for the last time before his execution in 1649. There are excellent sporting facilities at the Magnet Leisure Centre including ten-pin bowling and a 'Crystal Maze' adventure, but plans for a local museum have not yet come to fruition.

Maidenhead Bridge is an elegant 18th century affair, while the more stark Railway Bridge, designed by Isambard Kingdom Brunel, was hailed as a masterpiece when new. Both cross the Thames at a busy extension east of the town centre, but one with delightful walks nearby along the riverside towards Boulters Lock.

Cox Green is Maidenhead's business area with much of the latest technology in evidence. It is also the site of some of the region's most ancient buildings. The Residential area is built upon a large Roman Villa, while two medieval manors stand on its southern edge. Ockwells is a medieval work of art: a private house whose garden is very occasionally (once a year if you're lucky) opened to the public. A third house, Shoppenhangers, is now a hotel. It is a fascinating architectural mix, built in the early 20th century from ancient parts of other buildings.

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