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A few comments from a roadie... Helmets Each manufacturer uses a different "last" (ie form) on which to build their helmets. I have a Giro head - Bell helmets just don't fit right. So try on different manufacturers. Gloves Too many nerve endings not to wear gloves even in the summer. Pedals You imply that road bikers use toe clips. Not for quite some time now. Water A big advantage of water bottles over camelbacks is that they are easier to use with hydration drinks, because cleaning camelbacks is such a pain in the butt. I do sometimes carry my camelback on long rides (say, 80+ miles). Road bikes There is no reason not to have a bike that is comfortable for you. Even a racier bike can be set up to be comfortable for 5+ hours for the vast majority of riders (with a little training), and there are lots of touring bikes that are more comfortable. Having somebody do a bike fit for you is a very good idea. WRT your assertion about climbing. Even if it...