You’re on the right track with plans to partake of the Oregon Shakespeare Festival, Ashland’s claim to fame. If you haven’t already, see the Mail Tribune newspaper’s guide to the festival for news and reviews.
If you want to take in the region’s primary natural wonders, plan a day to visit Crater Lake, Oregon’s only national park, or Oregon Caves, the state’s first national monument. I always recommend both, but they are several hours’ drive apart. Here’s a recent story from the Mail Tribune to help you decide.
You could spend a couple of days on wineries alone. The Rogue region boasts dozens between Ashland and Medford, known as Bear Creek Boutique Wines. The Applegate Valley has its own “wine trail,” as does the Upper-Rogue region. See the Mail Tribune’s complete guide to wine tasting, as well as local wine coverage by columnist Janet Eastman.
Ashland has a few popular breweries, including Standing Stone and Caldera, but the up-and-comers are in Medford. Check out Southern Oregon Brewing and Walkabout, which is opening its taphouse in July. While you’re in Medford, eat at Downtown Market Co., the town’s No. 1 restaurant on TripAdvisor and one of my personal favorites.
Most of my “locals-only” tips center around food and dining. Ashland is replete with restaurants, particularly around the plaza, but some of the best (and more affordable) dining is removed from the downtown core. I always make a point of eating at Morning Glory for breakfast, Happy Falafel for a fast, inexpensive lunch and a newcomer, called Sauce, for really flavorful, healthy food.
It sounds a little strange, but Ashland Food Co-op in the railroad district does more food-service business than anywhere else in town. It has a salad bar, hot bar and deli that’s fresh, fast and can accommodate any type of diet.
Check out all my Ashland-area dining coverage here.