The Winchester Inn (35 S. 2nd St., 541/488-1113 or 800/972-4991, 5:30–9 p.m. daily, brunch 9:30 a.m.–12:30 p.m. Sun., dinner $15–26, brunch $8–13) is not only a renowned B&B but a first-rate dinner house as well. The Victorian dining room in this National Historic Landmark may look out on an English garden with a gazebo, but modern sensibilities permeate a seasonal menu that includes dishes such as grilled salmon with blackberry chipotle sauce and rack of lamb with sweet potato galettes.

The Peerless Restaurant (265 4th St., 541/488-6067 or 800/460-8758, 5:30–9 p.m. Tues.–Sat., $9–30) is part of a picturesque historic hotel; the garden is spectacular, so dine alfresco if possible. The impressive selection of small plates ($6–12) makes casual dining fun and exciting—start with duck confit–stuffed dates or lamb meatballs with blue cheese filling, and keep the plates coming. The menu also offers à la carte fine dining (salmon, steaks, pasta), but you’ll find it hard to resist the small plates.

Amuse (15 N. 1st St., 541/488-9000, www.amuserestaurant.com, 5:30–9 p.m. Wed.–Sun., $18–30) is Ashland’s top French-via-Northwest restaurant, with a menu that changes weekly and features fresh local fruit, vegetables, and mushrooms as well as ranch beef and lamb and locally harvested fish. Expect such sophisticated dishes as crispy veal sweetbreads with roasted mission figs or black truffle–roasted game hen. Desserts are especially good. The small dining room is deceptive; the back patio is shady and expansive.

Just down the road from Ashland is the absolutely unique New Sammy’s Cowboy Diner (2210 S. Pacific Hwy., 541/535-2779, dinner 5–9 p.m. Thurs.–Sun., $18–28). The chef-owners are Bay Area refugees who moved to Ashland with retirement in mind but somehow got talked into cooking for friends, then for the public, a few nights a week. The menu changes frequently, but expect delicious fish, rabbit, pork, and charcuterie, all prepared with great care and skill—if the braised beef ribs are offered, by all means order them. The wine list is very imposing, with hundreds of choices. The dining area is newly expanded, but to understand why New Sammy’s has such a devoted following, ask to be seated in the old dining room with cow wallpaper and just six tables in what was once a gas station. Call for winter hours; reservations strongly recommended.