The race is held every Easter over a course of 125 miles (201 km) from Devizes in Wiltshire to Westminster in central London.
Starting at Devizes wharf, the route follows the Kennet and Avon canal for 54 miles to Reading, where it joins the Thames.
Personalities to own a DW medal include former leader of the Liberal Democrats, Paddy Ashdown; explorer Sir Ranulph Fiennes; TV presenter Steve Backshall; Olympic gold medallist rowers James Cracknell and Helen Glover; adventurer Sarah Outen; and the first British woman to climb Everest, Rebecca Stephens.
The race follows the Kennet and Avon Canal for 52 miles (84 km) from Devizes through Pewsey, Hungerford and Newbury to Reading.
The event generated much interest, with some national press coverage, and a large crowd gathering at Westminster Bridge to see the end of the feat, which was completed in 89 hours 50 minutes.
In view of the interest shown, Frank Luzmore, one of the competitors from Richmond Canoe Club, decided to organise the event as an annual contest.
Albert Weibel, another member of the Richmond Canoe Club, donated a trophy for the winner, and at Easter 1950, 17 boats took part in the first official race.
As the main race soon became a one-day event, rather than a four-day one, much of the official kit was redundant, and there was widespread breaking of the rules.
[3] The original rules published in 1950 states "The Cup may be competed for by any canoeing team without restriction of age, its members must be normally resident in the British Isles."
The stage race, started in 1953 was introduced by the first more formal organisation to prevent Junior crews attempting to complete the course non-stop.
A junior / veteran class was introduced in 1989, with the intention of giving parents an opportunity to paddle with their children.
This non-competitive class is also free from the restriction of overnight camping within 200 metres of the course, allowing the use of hotel and B&B accommodation.
[5] In 2018, heavy rainfall prior to the Easter weekend and throughout Good Friday again brought the River Thames up to flood levels with fast-flowing water.
The race committee initially ruled that no night-time paddling should occur on the Thames, but after conditions worsened they decided that all classes would finish at Reading (Wokingham Canoe Club at Dreadnought Reach).
[9] In 2022, the event was shortened to 108 miles and finished at Teddington, since the grounds of St Thomas' Hospital were occupied by a vaccination station.
[12] In the event, high water levels from Storm Nelson led to parts of the canal overflowing, reaching Richmond.
The current (non-stop) course record was set during an unprecedented race in 2023, which saw half of the senior entrants disallowed by a competency-based assessment for safety reasons.
[14] For the staged events, the solo record was set in 1993 by G Butler of Nottingham Kayak Club in a time of 14 hours 46 minutes.