When one of my grandkids was around that age we pushed her up Red Hill in one of those strollers. My son and I took turns pushing it. It's rugged in places, but we did it.
I was thinking that Mt Shaw, above Castle in the Clouds (off route 171), might be an easier one, as much of the trail up from near the Castle is basically an old horse path and maybe is used by 4-wheel vehicles these days. What I don't know is how bad the lower end of that trail is for a stroller. You probably could Google the trail system to find out.
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