The Shakespearean Festival is Ashland's biggest draw, but not to be forgotten is the Cabaret Theater in the Old Pink Church. Laughter and music are the trademarks of their productions ($21-$30 per person), and you can dine before the production, have dessert during intermission, or just enjoy a bottle of wine during the entire fun evening. "Five Guys named Moe" is the current production.
There's lots of upscale dining in this college town as well. Amuse and Peerless are my favorites. In addition, Ashland is a great starting point for some wine touring.
