Tuhia he haere tonu mo tenei whitianga - I whakatuhia a Chepstow Town F.C. i te 1878 a mai i te tau 2017 kei te takaro i te Wahanga Tuatoru o te Welsh Football League. I whakatūria hoki a Chepstow RFC i te tau 1878, e ngā ākonga me ngā kaimahi o Chepstow Grammar School. Ka takaro nga whakataetae ki te Upton Memorial Ground, Lower Western Avenue. Mai i te tau 2017 kei te takaro te kapa i te Wahanga Tuatoru Te Tai Rāwhiti A o te WRU National League. Kei te taone ano tetahi Karapu Hakinakina mo te kopere (St Kingsmark Bowmen), teneti, peihana, kirikiti me te whutupaoro rangatahi. Ko te 1976 IAAF World Cross Country Championships
, i wikitoria e Carlos Lopes, i tu ki te taone nui. E rua nga huarahi roa o te Whatunga Pahikara a Motu ka tiimata i Chepstow, tae atu ki te Celtic Trail (Lôn Geltaidd). I whakahaerehia hoki e Chepstow nga huihuinga pahikara huarahi ngaio me ngaio, penei i te Chepstow Grand Prix.