Home of the Oregon Shakespeare Festival, Ashland, in Jackson County, is full of cultural opportunities. There are also nine other theatre groups, featuring a wide variety of performances, including musicals, comedy and experimental theatre. Shakespeare is always presented in the Oregon Shakespeare Festival's outdoor Elizabethan Theater and other plays are offered in the Angus Bowmer Theatre or the Black Swan. Music is everywhere in Ashland, with opera, bluegrass, folk singing and chamber music being only some of the offerings for visitors.

In addition to the wide variety of cultural offerings, Ashland has many forms of recreation. Skiing Mt. Ashland is a popular wintertime activity. There are 23 ski runs, 80 miles of cross country trails, and, best of all, it's only 15 miles from downtown Ashland. Ashland, built on the banks of Bear Creek, also has the Bear Creek Bike and Nature Trail. A favorite of bikers, the trail runs along Bear Creek, then down the valley to Medford. There is river rafting and jet boat rides on the Rogue and Klamath Rivers, and many pristine mountain lakes for anglers to try their hand at catching steelhead, salmon and trout.