Pedzisa mutsara unotevera: Chepstow Town F.C. yakavambwa muna 1878 uye kubva muna 2017 inotamba muChikamu Chechitatu cheWelsh 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. Nhamba
1976 IAAF World Cross Country Championships, yakakundwa naCarlos Lopes, yakaitirwa 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.