In all our time in the Pacific Northwest, we had never been to Medford or Ashland, Oregon. They are nice towns located 26 miles apart on Interstate 5. Together, they form sort of a “right brain/left brain” pair. Medford is a working man’s town. Here you will find all the franchise big box stores, from Costco to Walmart to Office Depot. It has a mix of an urban and rural mix, with working farms and vineyards located just outside the urban bustle. Reminds me of Spokane in that way.
Ashland is the nearby artsy town. Think Taos, New Mexico, Sedona, Arizona, or maybe Leavenworth, Washington. The economy of Ashland revolves around the Shakespeare Festival. Now more contemporary than Elizabethan, this has grown to an almost year round event that has branched far beyond Shakespeare to include any and all types of live theater.
Set in the beautiful mountains just north of Siskiyou pass (highest point on I-5), Ashland is filled with upscale shops that are the antithesis of the big box stores. Here you will find microbreweries with gourmet offerings that would attract any foodie, art galleries, and even a store specializing in Moroccan house furnishings.
Like many places, fall is a perfect time to visit both places, as you can see by the pictures below.