World renowned with lots of plays to see. The Elizabethean Theater is always a fun venue to see a play, as it is a large outdoor theater. If you do want to see a play, get dinner reservations in advance. There are many great restaurants in Ashland but during the summer if you do not have a reservation it will be hard to get into a restaurant before a play. All evening plays start at 8:00 pm.
If you want a wonderful evening under the stars, with music and good food, the Britt Festival in Jacksonville (20 minute drive from Medford or Ashland) is a beautiful setting to see a concert. And if you really want "Something to talk About" Bonnie Raitt is performing on June 3rd the Wednesday before our wedding. Parking is easy, there is a free lot with a shuttle up to the concert area or you can park in the small town and walk up. There are several good restaurants, wineries and small shops in Jacksonville that can make your night special. Lawn seats are cheaper and fun - just bring a blanket. You can rent lawn chairs and buy dinner at some of the up scale food trucks there if you wish. They also sell any beverage option you desire. It is also right up the street from where Grant and I first became friends and talked for hours after cross-country practice in high school!
This is where we went for our first date, many dates after and eventually where we went right before the proposal! Everything here is absolutely delicious! My go to order during the summer is the lemonade along with some type of treat. Grant loves their mocha and ordered it on our first date, I had a hot apple cider. The cream puff and lemon meringue tart are a couple of our favorites!