Pre Covid, I went to Ashland every fall. It’s a beautiful time to be there. Some places I like to stay are Ashland Springs Hotel and The Winchester Inn. The smaller bed and breakfast we like seems to be closed.
Amuse is great if you want an intimate fine dining experience. I make sure to go there every trip. Alchemy, in the Winchester Inn, is a good one, too. For something more casual, I like Standing Stone Brewing or Larks.
Safe travels!