I rode our mare on the roads all the time when we were kids. It was the only way we could go for a ride in the woods a few miles from our houses. Our horses were all barefoot. I actually rode so much that Lady didn't need her feet trimmed. Think about that for a second...
Now I don't ride that much (too bad), but also don't ride on the roads here much either. Basically because there is no shoulder to get off onto, and I live on a backwoods State HWY now... :(
I've learned to trim my horses hooves, and before I got stuck in the rut of doing a plain pasture trim, and Natural Hoof Trimmer taught me how to do a barefoot trim. She later gave me a DVD of her demonstrating how to do it when I brought home a rescue mare.
I am not good at explaining, but I could show someone how. I use a Hoof Jack that cost about $125 or $150. My nippers and rasp are old, but, we've sent the nippers in to be sharpened. The hoof knife is second hand too. So you don't *have* to spend a whole lot of money to get started. Most trimmers are more than happy to talk your ear off about how and what they are doing and tell you why.
My back isn't the greatest anymore, so when it is hurting I make sure to get either just the fronts or just the rears done. That way the horse is balanced. I'll go back out in a day or two and do the two that still need trimming. Most of the time I can get through all four feet. But only one horse a day!