Daggerfall runs well in DOSBox (which it hasn't always done) but I would not try running it in just the dos prompt in Windows.
Daggerfall was probably the largest RPG ever made, and there may never be a larger one ever. How is that possible? Well, the screen resolution is half VGA, and almost everything is stock rather than unique. The hundreds of towns and villages are put together - probably by a computer - from stock parts that can include whole shopping districts or single houses, slapped together in a random fashion. Likewise the humongous caves were made from stock parts that were chained together. Yet the variation is large enough that only the most dedicated players would remember all the stock parts in his head. The most dedicated player could have been me, but most likely it was one of my friends on alt.games.daggerfall. Perhaps the guy who thought he might go to Daggerfall when he died, instead of Heaven or Hell.
In any case, I have never seen a game in which you were so much in control of your own fate, and could choose to be a truly unique character. It was a big part of my life for many years and probably had some influence on my current thinking in various subtle ways.