The Hockley Viaduct was constructed in 1890 by the London & South Western Railway (L&SWR), led by its Chief Engineer, W. L. Galbraith. Originally known as the Twyford Viaduct, it crossed the River Itchen and its water meadows to link the Didcot, Newbury and Southampton Railway (DN&SR) to the LSWR's main line. The DN&SR had been scheduled to track the Itchen to Southampton, but a shortage of funding had terminated the line at Winchester.

The line was opened in October 1891 and was worked by the L&SWR from Southampton to Winchester Chesil station. A Great Western Railway (GWR) locomotive took over the haulage north to Newbury & Didcot, also working the DN&SR  under contract. After the grouping of railways in 1923, the L&SWR became part of the Southern Railway and GWR locomotives were permitted to through work into Southampton Terminus station.

The line was closed to passengers in 1942, whilst it was doubled between Didcot and Newbury, rebuilt and re-signalled to Winchester to carry the military traffic for the invasion of Europe. In the year prior to D-Day, sixteen thousand trains crossed Hockley Viaduct’s single track, joining the main line to Southampton at Shawford Junction and onto the new loop line to Eastleigh. A new link line was constructed just North of Winchester from the existing Southampton to Basingstoke line. Passenger services from Newbury to Winchester and Southampton ceased in March 1960 and freight services ended in 1966. The section of line from Shawford Junction across the Viaduct through Winchester Chesil Street to the tunnel under Winnall was purchased by Winchester City Council.

The pleasing, if relatively plain, structure comprises thirty three spans. It's external appearance suggests a brick construction but was in fact built with a solid concrete core in each pillar. Each pier weighs some 590 tonnes (650 tons). The bricks for the facing were sourced from the nearby Blanchards Works at Bishop's Waltham. The contractor was Jos T. Firbank. This method of construction was only confimed by test borings in 1996, making it amongst the earliest complex engineering structures to have a solid concrete core and a first for large railway viaducts.

Despite a number of attempts, the viaduct has not been Listed. While the ownership is complex - the structure is owned by Winchester City Council, standing on land owned by Hampshire County Council - the viaduct is to be acquired by Sustrans for integratation into Britain's 16,000 km (10,000 miles) long National Cycle Network.