I would be looking at a performance hybrid bike myself, Charles. They are great for both urban style riding and your paved trail riding...many can handle moderately maintained unpaved trails too. I've used my Jamis Coda Elite for years in town and on unpaved, somewhat bumpy trails with no issues. Performance Hybrid bikes are kind of a combo of city bike(gearing, 700c tires) with a mountain bike style frame(upright riding position, straight bar). $300 would be around entry level on one of the non-dep't store bikes, I believe.

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