3:00 p.m. Arrive in Ashland. Check into your hotel or inn of choice. Stroll through 93-acre Lithia Park, designed in 1917 by Golden Gate Park architect John McLaren, with miles of walking trails along rushing Ashland Creek with Japanese Gardens, grassy glades, duck ponds and more.
6:00 pm - Dinner and a show at the always entertaining Oregon Cabaret Theatre, located on the corner of First and Hargadine Streets in the fully restored Old Pink Church. This uniquely inviting ambience delivers first-rate musical entertainment year in and year out.
10:00 am - Take a backstage tour at the Oregon Shakespeare Festival and go behind the scenes at America's largest rotating repertory theatre company
Suggestion for lunch: Creekside dining along the banks of Ashland Creek on Calle Guanajuato in the heart of Ashland.
2:00 p.m. Tour Ashland’s Historic Railroad District with art galleries , shops, parks, yoga studios, bike rentals and more.
3:00 pm - Indulge yourself at one of Ashland's many spas or salons. Treat yourself to massages, facials, saunas and more.
6:00 pm - Dine at one of the 100 restaurants Ashland has to offer. From sushi to Italian to Northwest cuisine and more, cosmopolitan Ashland is a foodie's delight that offers more choices than you couls savor in a week.
8:00 pm - Attend a play in one of three unique theatres at the Tony Award-winning Oregon Shakespeare Festival.
8:00 am - Embark on a half-day rafting trip on the exciting Rogue River from downtown Ashland--be back in town after lunch.
1:00 pm - Visit delicious artisans such as Dagoba Chocolates or Branson Chocolates. Or experience one of Ashland’s award-winning microbreweries like Caldera Brewing Company or Standing Stone Brewing Company. Or venture out on the Bear Creek Wine Trail to enjoy some of the wineries Wine Enthusiast Magazine named the Top Ten Wine Regions in the world last year.
5:00 pm - Shop the unique retail stores of downtown Ashland while you stroll through Historic Downtown Plaza in search of yet another fabulous dinner spot.
6:45 pm - Attend the free outdoor Green Show at the Oregon Shakespeare Festival on the Courtyard Stage on the Bricks.