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1944–1945: Establishment

Workington Town RLFC was formed at a meeting held in the Royal Oak Hotel, Workington in December 1944. Many of Workington Town's board came from local football team Workington AFC's board and the team would ground share with "the Reds" at Borough Park. It was decided at the meeting that the club should be registered as a business and that an application for membership of the Rugby Football League should be submitted. From those in attendance at that meeting the first board of directors was formed and the application for membership was agreed at a meeting held on 23 January 1945 at the Grosvenor Hotel, Manchester. They were the first side from Cumberland to enter the professional rugby league.

They first played their home games, wearing green and red hoops, at Borough Park. The first match against Broughton Rangers on Saturday 25 August 1945 attracted a crowd of 4,100 to Borough Park. Workington went on to win 27–5.

In their first season, they achieved the distinction of losing to an amateur side, Sharlston Rovers in the first round of the Challenge Cup, a very rare occurrence in those days. However, the first round was a two leg affair, and they were able to make amends in the return leg and progress to the second round.

1946–1969: Golden era

Gus Risman joined Workington Town as player-coach in August 1946 when they had been in the Rugby League for only one season. In his eight years at the club, he made them into a team capable of beating Wigan or anyone else in the league. There was a club record 20,403 for the third round cup game against St. Helens. Town finished third of 29 clubs but had a tough draw; the only Yorkshire teams they played were Bradford, Leeds, Halifax, Keighley and York. They played these five home and away as well as all the teams from Lancashire. All the top four that season were all from the Western side of the Pennines and Workington went on to become rugby league champions in 1951. After beating reigning champions Wigan by 8-5 away at Central Park in the play-off semi-final, Town became champions themselves for the one, and so far only, time by beating Warrington in the final held at Maine Road, Manchester by 26-11. Warrington raced into an early 8-0 lead after 30 mins before a try from Paskins and 2 tries each from Gibson and Wilson, supplemented by 3 goal kicks from Risman, brought the title to Cumbria.

The following season they then beat Featherstone Rovers 18–10 in front of a crowd of 72,093 at Wembley Stadium to become Challenge Cup winners; this was the first final to be televised. No other club, before or after, has lifted both these trophies within such a short period of their formation. During the 1954–55 season, Workington Town made it to the Challenge Cup final but were beaten 21–12 by Barrow. Owing to tension between the football club's manager Bill Shankly and the Town manager, Gus Risman and director Tom Mitchell, Town moved out of Borough Park in 1956 and took a 150-year lease on the land at Derwent Park and built a new stadium.

Workington Town lost in the 1958 Challenge Cup final to Wigan and one week later, they lost in the Championship final at Odsal Stadium, Bradford.

In 1962, the league was split into East and West of the Pennines; Widnes and Workington Town met at Central Park, Wigan, in the first final of the Western Division Championship on Saturday 10 November 1962. With two minutes remaining, Syd Lowdon dropped a goal to earn Workington a 9–9 draw. Later in the month Workington won the replay 10–0.

The record attendance at Derwent Park was set in 1965 when 17,741 spectators turned up for a third round Challenge Cup match against Wigan.

1970–1995

The early 1970s brought demise of Town as a power in the game and the fans dropped off making it very difficult for the management to come up with the cash to bring in top class players who were being enticed out of the county to other clubs. Paul Charlton took over as player-coach in 1975 and guided them to promotion. Local players returned to the club and a team consisting mainly of home grown players started to bring back glory to the Town by appearing in a Lancashire County Cup Final in October 1976. They appeared in a further three finals in consecutive season winning the trophy by defeating Wigan in the 1977 final.

The last of those four finals was staged at Salford's Willows ground on Saturday 8 December 1979, and attracted a crowd of 6,887. Widnes were firm favourites to lift the cup and held the Cumbrians at bay to register an 11–0 victory. Probably as a result of the three previous finals, several top class forwards caught the eye of the wealthy Lancashire clubs who enticed them away from Derwent Park.

Tommy Bishop was coach between 1981 and 1982. The 1980s were the lowest era in the club's history as it saw Town mainly as a yo-yo side going in and out of the first division but mostly wallowing halfway down the second. During this period, the fan base practically disappeared, and as the 1990s arrived it was third division rugby status.

Peter Walsh joined Town as Head Coach in the summer of 1992. Town were beaten finalists in the 1992–93 Divisional Premiership going down to Featherstone Rovers while in the Third Division. Workington won the Second Division Championship and Divisional Premiership trophy double in 1993–94, the Divisional Premiership was won over London Crusaders at Old Trafford, Manchester. That took them into the top flight of rugby league and Town finished ninth in the Stones Bitter Championship. Peter Walsh quit as the coach of Workington Town to return to Australia in July 1995.

1996–present: Summer era

When the Super League was set up, it was proposed that Workington merge with Barrow, Carlisle and Whitehaven to form a Cumbrian super club to be based at Workington. This was, however, resisted and an unmerged Workington took part in Super League but would record only two wins all season. They finished bottom of the table and were relegated to the Northern Ford Premiership with significant debts.

In 2002 Town dropped into National League Two as a result of losing to Dewsbury in what was the fore-runner of the National League Two Grand Final. Billy McGinty took over as coach on 25 May 2003.

In 2003, Ged Stokes was in charge of the New Zealand A-team on their tour of England. At the end of the tour, he was offered the vacant coaching job at Town. Workington were at a low ebb and had only seven players in their squad.

A Challenge Cup game against Leeds brought a large crowd that allowed the club to clear their debts. Assistant coaches Craig Barker and Les Ashe took over and led the team to the Elimination Semi-final but they were defeated by Oldham. A few weeks after Town's 2007 season had come to a close, Town appointed Whitehaven coach Dave Rotheram as their new coach. In Rotheram's first season in charge Town finished eighth in National League Two with only six wins from their twenty two games and were eliminated in the first round of the play-offs at Keighley.

Following a poor start to the 2009 season, with Town only gaining two wins up to that point, Dave Rotherham decided to step down. He was replaced in July 2009 by joint coaches Martin Oglanby and Gary Charlton.

2011 was a much better year with Town reaching the 2011 Championship 1 Grand Final by defeating Keighley 19–10 in the elimination semi-final. In 2021 Workington were promoted to the English Rugby League Championship, with a 36-12 win over Doncaster in the League 1 play-off final. In Workington Town's first game back in the Championship, they were defeated 20-6 by Newcastle Thunder. In the 2022 RFL Championship season, Workington Town were relegated back to League 1 after finishing bottom of the table. Workington managed to win only one match for the entire year. Workington finished the 2023 League 1 season in 5th place.