Why not visit Gloucester and after 10 minutes walking rounds the cross (in the middle) you will see the type of customers you need to aim a pub at. (under 20, push chairs, kids, chavs, unemployed, homeless etc.)
I have lived in Gloucester all my life and hate the city centre. I will always go out in Bath or Cheltenham for a night out as Gloucester is a dive!
Cirencester is a better option but you will find lots of their residents go to Bath and there is not much of a riding scene.
Cheltenham is the place for you but be prepared for high rent charges.