“Roughly halfway between San Francisco and Portland, the foothill town of Ashland tends to attract ex-urbanites who have tired of city life but don’t want to let go of culture entirely. With its many art galleries, thriving food scene, theaters and the resources of Southern Oregon University, Ashland’s offerings satisfy eclectic tastes. The world-renowned Oregon Shakespeare Festival put the town on the cultural map in 1935 and is now a more or less required trip for theater buffs from all over the country.
Less well known are the relatively newer Ashland Independent Film Festival, which takes place every April, and the Oregon Chocolate Festival, which showcases delectable creations from around the state. For more low-key activities, time your visit for the first weekend of the month and join the locals in the First Friday Artwalk, when Ashland’s dozens of galleries stay open late, offering free food and music.”