The 20 Best Restaurants in Ashland, Wisconsin

Deep Water Grille combines a working brewery with a casual restaurant atmosphere in a distinctive historic-style building. House brews, including a signature nut brown ale and seasonal offerings, pair with hearty comfort fare such as local whitefish prepared in several styles and a popular beer-cheese soup. Guests note generous portions, fresh rolls, and house-made dressings, along with attentive, helpful service even during busy evenings.

Chequamegon Food Co-op Deli offers a clean, modern market environment focused on natural and healthy choices. Guests find fresh made-to-order and ready-made sandwiches, a well-regarded salad bar, and rotating hot specials such as local Lake Superior whitefish. Shelves are well stocked with regional products, including distinctive sodas, while attentive staff contribute to an easy, welcoming visit.

Pita Hut Big Ben's Famous Gyros is a casual, drive-up café specializing in generous, made-to-order gyros. Tender lamb and chicken are wrapped in soft, fresh pita with crisp vegetables and a well-regarded garlic sauce. Outdoor seating and a view toward the nearby harbor create an easygoing, food-truck-style experience that suits both a quick stop and a relaxed meal.

Ashland Family Restaurant offers classic American diner fare, from hearty breakfasts like omelets to burgers and comfort dishes such as chicken fried steak. Guests note a friendly welcome and attentive staff who stay on top of a busy dining room. The atmosphere suits all ages, with a simple setting that some find a bit dated. Diners appreciate the flexibility of side options, including salad, soup, fries, or fresh fruit.

2nd Street Bistro in Ashland offers classic bistro cooking with fresh, comforting flavors. Favorites such as butternut squash ravioli, regional whitefish, and hearty chowder show careful preparation and appealing presentation. The small, charming dining room and attentive, knowledgeable service create an inviting setting for a relaxed meal.

Culver's is a casual stop for quick meals and frozen treats, including popular concrete-style sundaes. Staff members are noted for their courteous, efficient service, even during busy periods. Outdoor tables and picnic spots behind the restaurant overlook the lake and Chequamegon Bay, offering a pleasant setting to relax and enjoy the view.

New China Restaurant serves classic Chinese dishes prepared to order, with hot, fresh flavors and generous portions. Guests highlight staples such as General Tso’s chicken, lo mein, and crab rangoon. The dining room is notably clean, with attentive, courteous service. Outdoor seating with views of Lake Superior and a full bar add to the relaxed experience.

Chequamegon Grill offers classic American grill favorites in a historic hotel setting with views and character. Diners highlight well-prepared dishes such as pan-seared whitefish, ribeye steak, and fried chicken, along with hearty sides and indulgent desserts like rich chocolate cake and creamy custard. Attentive, personable service and a comfortable dining room contribute to an enjoyable experience.