Suggestions for visiting cute small towns in the US

I recently went through a very rough time in my life and have experienced great loss. While I’m receiving therapy and healing, I am also becoming more aware of my inner self and creating an inner world that I am comfortable with without needing other people. I work remotely and have the option to work from anywhere. I have this want to visit cute small towns by myself and experience a different culture and locals than what I am used to. I also want and love cloudy weather and rain, and greenery and I don’t get much of that where I live in a desert. I would love to visit a place that gives me all of this while I heal and get comfortable with my inner self. Suggestions of towns with appropriate times of the year would be greatly appreciated. :)