Hey Dan, I know there is a few rider's in Weymouth, but you'r best bet is to get on the train and come to poole occasionally, it's about a 50 min journey prob cost you bout £10. You can also get direct trains to Bristol from Weymouth. If you fancy the ride/walk or you can get a lift, then you should go to Portland Bill whenever you can, the rocks there are amazing, you'll certainly love it and your'e natural riding will improve loads, plus some of the rocks are big flat edged ones so you can ride street on them. Weymouth i found to not have much to ride, but Portland does have plenty to ride, though it's all rocks there's a huge variety.