Chepstow plays host to a vibrant and ever changing night life.
The town has plenty of pubs and bars, and an assortment of local restaurants with a variety of cuisines.

Chepstow is also home to a perhaps surprising number of clubs and other outdoor and sporting activities.
There are a number of gyms available in and around town, as well as number of different clubs and associations for bowling, rifle shooting and athletics.
Chepstow also has it's own Rugby team.

Chepstow Racecourse is a thoroughbred horse racing course located just north of the town of Chepstow in Monmouthshire, Wales, near the southern end of the Wye Valley and close to the border with England.