OSF is a world-class theatre with multiple plays almost everyday. It's best known for its Shakespeare plays and its outdoor venue.
Wander around Ashland's 100-acre park. The park follows Ashland Creek through undeveloped woodlands and also includes a Japanese garden, two duck ponds, groves of sycamore trees, and a number of secluded spots. (Watch out for bears.)
If you have a car, the trailhead to Grizzly Peak is only 30 minutes outside of town. The trail is about 5 miles roundtrip and offers a beautiful lookout at the end.
The absolute best spot for breakfast and brunch in Ashland.
A beautiful winery for a glass of wine with a view just outside of town.