For those of you on the west coast, Ashland is definitely worth a visit. Ashland has a perfectly nice little airport, no problem for any Commander, although I usually go into Medford since it's only about 10 minutes drive and has a big runway, ILS, multiple good FBOs, rental cars, etc.
The highlight at Ashland is the Oregon Shakespeare Festival. It's some of the best theater you'll see outside of New York. They run most of the year (not in December or January, I think), and have three stages-- a big indoor stage, an outdoor classical stage, and a black box theater. They don't just do Shakespeare, although they always do a fair amount-- but they do lots of other plays as well, both modern and classical. They even usually have one or two plays which premiere there each year.
Ashland's downtown connects to Lithia Park, which is a beautiful park running up a little valley, with a nice creek running down the middle. There are a bunch of very nice restaurants in downtown Ashland, and some nice stores. It's a nice walking downtown.
One thing to be aware of-- Ashland is not dog-friendly, at all. That said, we typically bring our dog and seem to get by, but it is something you should know about.
Jacksonville, which is close by, hosts the Britt Music Festival in the summers. That is also worth a visit, if you're a music fan-- they get some pretty big acts, in all different genres from classical to country to rock.
