Nyorai kuenderera mberi kweiyi ndima - Chepstow Town F.C. yakavambwa muna 1878 uye kubva muna 2017 inotamba muDhivhizheni yechitatu yeWelsh Football League. Chepstow RFC yakavambwawo muna 1878, nevadzidzi nevashandi veChepstow Grammar School. Mitambo inotambwa paUpton Memorial Ground, Lower Western Avenue. Kubva muna 2017 chikwata chinotamba muDivision Three East A yeWRU National League Guta rinewo kirabhu yemitambo yekupfura uta (St Kingsmark Bowmen), tenesi, mabhora, kiriketi uye nhabvu yejunior. IAAF World Cross Country Championships ya1976
, rakundwa naCarlos Lopes, rakaitirwa mutaundi. Nzira mbiri refu dzeNational Cycle Network dzinotangira muChepstow, kusanganisira Celtic Trail (Lôn Geltaidd). Chepstow yakabatawo nyanzvi uye amateur mumugwagwa bhasikoro zviitiko, akadai Chepstow Grand Prix.