Ashland
Oregon Shakespeare Festival - In summer, kids will enjoy seeing innovative productions of Shakespeare plays in an outdoor setting, such as Romeo and Juliet set in 19th century California or Troilus and Cressida amidst a conflict in the contemporary Middle East. Plays are recommended for kids ages 10 - 12 and up, advance reservations are a must. Here's the schedule.
Lithia Park - The outdoor Shakespeare Festival theater is situated at the edge of Lithia Park, and the park itself is delightful for kids. Lovely playground, with climbing structures, swings (including toddler swings) and a sparkling stream, duck ponds (please don't feed the ducks), benches, shade and picnic tables - bring your lunch.
Daniel Meyer Pool (Hunter Park) - Days in Ashland can be warm. Cool off in the public swimming pool, plus wading pool for toddlers. Open June - Labor Day.