Before the First World War, in the summer of 1911, a "Pageant of Progress" was staged in Fromehall Park, Stroud, with 1,300 performers. Constance Smedley, the novelist, and her artist husband, Maxwell Armfield, were responsible for the dramatic work in the Pageant and according to one contemporary account, “there was only one rehearsal and the pageant went without a hitch”. Afterwards Constance Smedley formed a Committee to consider how plays could be brought to the villages in the area. The committee first met on 6th October 1911 at the Armfield’s house in Rodborough where they decided to set up an organisation that was to be called Cotswold Players. They gave their first performance in Amberley where there was “general and free prompting” according to the local paper and among the audience was Geoffrey Whitworth who later formed the British Drama League. The early plays they performed were simple situation comedies, often written in the Gloucestershire dialect and sometimes featuring local locations and legends. The Players toured their plays to the villages around Stroud, setting up stage at schools and village halls, often travelling considerable distances in all weathers, by bicycle and wagonette and even Shanks’s pony.

During the First World War all the profits from productions were given to war charities - profits which amounted to something over a thousand pounds. Most of this effort came from the lady members, and it was not until the end of the war when the men returned home that expansion occurred. In the early 1920s, Theodore Hannam-Clarke and John Masefield (later Poet Laureate) were very active with the Players, the former first as an actor and later as producer, and the latter as playwright, co-producer and later as President. In his book, "Drama in Gloucestershire", published in 1928, Hannam-Clarke refers to the Cotswold Players as "the most distinctive amateur organisation in the Country". This is borne out by contemporary references in the national newspapers.

Theatrical history was made in 1922 when the Cotswold Players became the first actors to take a play to one of H.M. Prisons, when they presented Jerome K. Jerome's 'The Passing of the Third Floor Back’ at Gloucester Prison. This unique occasion has since been followed by a more recent visit to Leyhill Open Prison.

Early in 1925, Galsworthy's 'Silver Fox' was presented by the Players in Bristol. This sets up an echo for latter-day Players when, in 1959, they won the National Tape-Drama contest with a scene from this play.

Under the conditions of the Second World War, the Players’ activities were necessarily limited. However, things returned almost to normal within a few months of the war's end. From 1945 until the early part of 1957 the Cotswold Players presented a series of successful play seasons at the Church Institute, Stroud. So spectacular indeed was the resurgence that in 1954 the Players were invited to perform their production of "Vanity Fair" before an international audience at the British Drama League Annual Conference and Theatre Week at Malvern. The adaptation - from Thackeray’s famous novel - was by Constance Cox, well known for her adaptations of the classic for television. She came to Stroud and accompanied the Players to Malvern. The reception accorded the play was most moving and Dorothy L. Sayers, who saw this presentation, stated "the production would have done justice to the professional stage". The Cotswold Players have many times been successful in competitions and festivals both in Gloucestershire and further afield.