Ashland, OR is just across the CA border on the 5 fwy. Home of the Oregon Shakespeare Festival & Southern Oregon University. The OSF season runs Feb-Nov, there are free Green Shows in summer. There are other theaters in town and nearby, and the university has music, dance and drama programs as well. The Britt Festival Pavilion hosts great concerts & the Medford Armory always has fun events.
Lithia Park, voted one of the best parks in the U.S. is right off downtown with hiking, biking, sports, a playground, a lake for swimming, ice skating in winter & bandshell concerts in summer.
Wonderful restaurants in Ashland! Beasy's On The Creek, Peerless Hotel & Restaurant, and Amuse to name 3 of the best. Other food of note: Callahan's Lodge and Restaurant, New Sammy's Cowboy Bistro, Puck's Donuts & Noble Coffee.
Ashland Springs Hotel with Lark's Restaurant on Main Street & the Lithia Springs Resort north of town are good hotel choices. There are many other hotels, motels & B&Bs available in Ashland or any of the neighboring towns.
Great wineries offer tastings throughout the Rogue, Applegate, Umpqua & Willamette Valleys: Weisinger's, RoxyAnn and Grizzly Peak wineries to name just 3.
Great hiking at Grizzly Peak Trail & Mt. Ashland Ski Resort. Take a day trip to Crater Lake.
Visit Jacksonville & Medford. Stop in Central Point at Lillie Belle Farms Artisan Chocolates & the Rogue Creamery cheese shop.
Visit my facebook page "Food, Wine and Theatre in Ashland, Oregon" for more info: