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Well, Avery Ranch is certainly hilly, and you have access to Parmer Lane and parts of western Round Rock without too much hassle. I've ridden from western Round Rock down Parmer into northern Austin many times, it's not too bad. I haven't done the Dam loop, so not sure about that.
I've lived in Round Rock nearly 15 years, and it isn't very bike or pedestrian friendly, in general. There are some ACA routes out in the surrounding rural area that are okay. There's also a group that rides out of Georgetown, the Georgetown Cyclopaths, and those routes are rural, have some rolling hills, and are pretty quiet, i.e. few cars.
Round Rock likes to call itself the Sports Capital of Texas (or something like that), but it isn't bike friendly. They also had a running race that they ran for 25 years and then dropped. Doesn't seem very sports friendly to me.
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