Chepstow Town F.C. was founded in 1878 and as of 2017 play in Division Three of the Welsh Football League. Chepstow RFC was also founded in 1878, by pupils and staff of Chepstow Grammar School. Matches are played at the Upton Memorial Ground, Lower Western Avenue. As of 2017 the team play in Division Three East A of the WRU National League The town also has an athletic Club for archery (St Kingsmark Bowmen), tennis, bowls, cricket and junior football. The 1976 IAAF World Cross Country Championships, won by Carlos Lopes, were held in the town. Two long routes of the National Cycle Network start in Chepstow, including the Celtic Trail (Lôn Geltaidd). Chepstow has also held professional and amateur street cycling events, such as the Chepstow Grand Prix.