As a 20-something living in Ashland, probably definitely expect to have to drive 15-20 minutes to Richmond to do something if you like going to places other than sports bars. My partner commutes to Richmond every day and it's not unbearable, but it's not really known for parties outside of the college. It's nice if you like the quiet, and the town does hold events pretty often by the railroad tracks or at the theatre, but it's really just a small town. I like the small town vibes, but I'm planning on moving closer to Richmond because there's not so much for me to do here.