A nice day trip from Ashland is Jacksonville, a national historic landmark that hosts the outdoor Britt Music Festival concert series into October. Or go on an artisan-food tasting tour in Central Point, home to Rogue Creamery and Lillie Belle Farms.
You could spend a couple of days on wineries alone. The Rogue region boasts dozens of wineries 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.