The antiquary John Leland claimed that the area around Maidenhead's present town centre was a small Roman settlement called Alaunodunum.

This villa sat on the route of the Camlet Way which was a Roman road linking Silchester (Calleva Atrebatum) and Colchester (Camulodunum) via St Albans (Verulamium) and passes through the present town centre.

Maidenhead's name stems from the riverside area where the first "New wharf" or "Maiden Hythe" was built, as early as Saxon times.

They disembarked from their longboats by the wharf and ferry crossing at Maidenhead and fought their way overland to Reading where they set up camp and made it their regional power base.

Previously, it had kept to the north bank and crossed the Thames by ford at Cookham, and the medieval town, later to become Maidenhead grew up on the site of Alaunodunum and South Ellington, between the new bridge and the bottom of Castle Hill.

[4] The new bridge and wharf led to the growth of medieval Maidenhead as a river port and market town.

Maidenhead also became the first stopping point for coaches travelling from London to Gloucester and Bath and the town became populated with numerous inns.

King Charles I met his children for the last time before his execution in 1649 at the Greyhound Inn[6] on the High Street, the site of which is now a branch of the NatWest Bank.

By Edwardian times, nearby Boulter's Lock became a favoured resort, especially on Ascot Sunday, and Skindles Hotel developed a reputation for illicit liaisons.

The Boundary Commission abolished this constituency for the 1997 general election since the electorate had become too large, splitting it into the new seats of Windsor and Maidenhead.

[16][17][18] The Royal Borough of Windsor and Maidenhead became a unitary authority in 1998 when it took over the functions of the abolished Berkshire County Council.

Bray village is linked to Maidenhead by the exclusive Fishery Estate which lies on the west bank of the Thames.

Maidenhead lies immediately west of the Taplow ridge, a wooded spur of the Chilterns which rises dramatically above one of the most scenic stretches of the Thames.

Maidenhead has a site of Special Scientific Interest (SSSI) in the northern outskirts of the town called Cannoncourt Farm Pit, where the largest hand axe of the paleolithic era in Britain was discovered.

[22] On 12 July 1901 Maidenhead entered the UK Weather Records with the highest 60-min total rainfall at 92 mm (3.6 in).

The church, consecrated on 2 December 1857 by Bishop Samuel Wilberforce, became the first ecclesiastical parish in the Borough of Maidenhead.

[25] Ten years later, in 1867, his brother William Wilberforce junior founded a Catholic chapel that led to St Joseph's Church.

[26] Maidenhead clock tower was built for Queen Victoria's diamond jubilee and stands outside the railway station.

There are also plans to demolish the 1960s Nicholsons shopping centre and replace it with a new retail and residential quarter built around a network of revived historic streets and a micro brewery.

Part of the scheme involves restoring the old Thames tributaries which run through a historic section of the town centre.

The redevelopment will bring an attractive waterfront quarter with new apartments, boutique stores, restaurants, bars, and cafes are to be a feature this new part of the town centre.

The adjoining historic section of the High Street around the 18th century Chapel Arches Bridge has been restored as part of the development.

The local authority also provides a Shopmobility service, where those with physical disabilities can borrow mobility scooters to navigate around the town.

Maidenhead Heritage Centre and Museum was established in 1993 and moved to permanent premises in a former pub in Park Street[31] in 2006.

The Brunel-built Great Western Main Line and the 21st-century Elizabeth Line pass through the town, calling at Maidenhead station and offering direct services to London (Paddington and intermediate stations towards Liverpool Street, Shenfield, Canary Wharf and Abbey Wood), Reading, Didcot, and an hourly direct Sunday service to Swindon.

However, after consultation, Crossrail Limited and Transport for London decided to extend this to Reading, which also serves as a major hub for the Great Western route.

Two miles to the south-west of the town lies White Waltham Airfield, a base for general aviation and flight training.

The closest higher education institution is Buckinghamshire New University in High Wycombe, 14.5 km (9 mi) to the north.