Taunton - Bleak. Only time I've ever seen someone smoking heroin was under a bridge here whilst out on a bike ride.
Liverpool - Only ever been here for football at Goodison and Anfield so probably not the best way to visit. That bit round Anfield with all the derelict houses is so depressing. Always seem to end up in the Lutine Bell with Scousers wanting you to tell them how amazing their ground is.
Riga - Stag central. Horrible.
Pitsea, Essex - lots to choose from in Essex, but Pitsea is probably the worst I've visited.
Wroclaw - the most boring place I've ever been to, and had to kill 2 days here for a wedding