One story above Ashland Plaza, the Black Sheep Pub and Restaurant (51 N. Main St., 541/482-6414, 11:30 a.m.–1 a.m. daily, $8–24) is a vast Olde English pub with better-than-average pub fare plus a wide selection of British and Northwestern ales. This is the place to come for a late-night after-theater supper (burgers, steak pie, grilled salmon) with frothy pints of beer.
Bright, airy, and with a delightful back patio open in good weather, 
Standing Stone Brewing Company (101 Oak St., 541/482-2448, 11:30 a.m.–midnight daily, $8–19) has one of the most pleasant dining rooms in Ashland [1]. Not only are the beers tasty, the menu is very broad, including soup, salad, burgers, wood-fired pizza, and entrées verging on fine dining.
Links:
[1] http://www.moon.com/destinations/oregon/southern-oregon/ashland