S.H.
We have a Kidarooz bike trailer that is also a stroller. It fits two small kids and has a handlebar for pushing that can be taken off if you attach it to the bike. We do use it for biking sometimes, but it has been to the park for walks and hikes on dirt trails many a time. The front wheel is removable for biking as well. The two main wheels are large in diameter, which really makes for easy pushing. Much easier than a standard stroller. It doesn't really get smaller, so that isn't a plus for your wants, though. It is moderately lightweight and has rear wheel locks. We have been very pleased with our purchase, although I think it was more that what your price range is. Just another option, though. Good luck!