Thanks for your question! Of course, ‘best’ is a subjective term, but I’m happy to give you my personal recommendations for Ashland and Medford restaurants, as a local. There are many we love!
In Ashland, I highly recommend checking out Brickroom for an upscale pub-like atmosphere; their cocktails and appetizers are their strongest suit, so they’re a good happy hour location as well. For a fine dining experience, Amuse gets my vote (it’s down in the Railroad District), and if you want the largest wine selection, Liquid Assets is a cozy wine bar right by the park.
You also can’t go wrong at Lark’s, located in the Ashland Springs Hotel. They’re another excellent cocktail location. For casual fare, check out Flip, a simple but delicious burger and fry place by the park…they’re owned by the same family as Amuse. Martolli’s is another solid causal dining option.
In Medford, our favorite pub and pasta place is Porters, located in an old railroad depot. They have a great happy hour menu with sliders, salads, and the like, and excellent cocktails. Lark’s also has a Medford location now, located in the Inn at the Commons. There are several fun breweries in Medford, including Walkabout and Bricktowne. Here’s a pretty comprehensive list. I also recommend Jasper’s burgers on Highway 99 between Medford and Central Point.
Hope this list gets you started!