Home to the oldest full-scale Elizabethan stage in the Western Hemisphere, Ashland's Shakespeare Festival is a wonderful way to spend an evening (or two!). Buy your tickets early or pack a picnic to go to the Green Show, a free performance on the bricks every evening before the plays begin.
Catch an outdoor concert in historic Jacksonville, OR — named one of America's top 10 coolest small towns by Frommer's.
Raft, kayak or fish the Rogue or Upper Klamath Rivers!
Hike beautiful Grizzly Peak! One of many hikes in the area.
One of many award-winning and picturesque wineries in the region. Here's a few more the SF Chronicle recommends: https://www.sfchronicle.com/travel/article/Five-vineyards-you-must-see-in-Oregon-s-12937638.php
Ashland's most famous and widely distributed brewery.