Founded in 1878 Chepstow Town FC is the most easterly of all Welsh
League clubs. Formerly known as Chepstow Castle FC home fixtures
have been played at various venues around the town from Bulwark to
St Arvans and also at St Mary’s institute ground which is where the
Tesco supermarket is now located.

Up to the beginning of the First World War all matched played were in
the local East Gwent League but with the resumption of football after
the war the 1919 – 20 season saw Chepstow Town become cofounders
of the Welsh League.

Welsh League football was enjoyed until the mid 1920’s which then saw the club relegated to the Mon County League. In 1928 the club then entered the Gloucestershire Northern Senior League and they became league champions in the 1931 – 32 season. Home matches during the club’s time in this league were played the St Mary’s institute ground.

During World War Two the St Mary’s ground was taken over by the Ministry Of Defence and used as a supply depot for the war effort.
At the end of the war, returning local servicemen wanted to revive
football in the area. The club was then reformed incorporating
Chepstow Boys Club and Fairfield football team and rejoined the Mon County League.

In the immediate post war years Chepstow FC became the dominant
club in the area and it was not uncommon for crowds of 200 to 300 to
watch the club’s matches.

The period of the mid 1950’s to the mid 1960’s was one of great
success for the club, on and off the field, and this was rewarded with
promotion back to the Welsh League culminating with the team
becoming Division 2 champions in the 1964 – 65 season. Regrettably
due to the high cost of travelling expenses and financial difficulties the club were forced to drop out of the Welsh League.

Chepstow Town then joined the 3rd Division of the newly formed Gwent Premier League and quickly advanced to gain promotion to the 1st Division.

Due to Chepstow Council’s road expansion plans and the proposed redevelopment of St Marys the club was relocated to the present
Larkfield Park ground in the late 1980’s. In 1997 the club were
promoted to the Welsh League and remained there until being
relegated back to the Gwent County League in 2007. Despite this
setback Chepstow Town were determined to regain Welsh League
status and this was achieved last season with the club finishing as
Gwent County League champions.

Over the years Chepstow Town has been graced with some notable
managers including Brian Harris (Everton and Cardiff City) and Barry
Vassallo (Arsenal and Plymouth Argyle). Chepstow Town players who
became professional footballers were Ollie Burton (Newport County,
Norwich, Newcastle and Wales), Colin “Rocky” Hudson (Newport
County and Cardiff City) and Harry Harris (Newport County,
Portsmouth and Wales.