Charlie was EXACTLY the same. It just took LOTS of time...it was about 7 months before we started seeing less problems. Carring a fully grown cocker past a scary jet wash isn't ideal...but we've persevered. Now it's amazing seeing the transformation from scaredy puppy to big brave boy (he's 2 soon). However, even now, if there is something scary he'll run past it, or make a wide berth of it, or if dogs are barking he'll speed past them...but we can deal with that.
Charlie however, still doesn't like going out in the wind and will pull on this walk to get home quicker.
When he was little, he wasn't too good in the dark either (even in the garden) so I used to sit on the back step with him (in October) at night, with him on my knee cuddling him and just talking to him. Just so that he relaxed and realised there was nothing to bad out there.
We also have a very popular dog walking area about 20m from home...he refused to go up there and 99% of the time he'd refuse to go up it...so we just avoided it, and used to walk back down it (which was ok)...however, it's only recently he's actually brave enough to walk up it and even still, it's rather slow.