Favorite Restaurants & Pubs
Ashland Wisconsin

Deep Water Grille Ashland WI
The Tap Room of Ashland's South Shore Brewery & Deep Water Grille

Our favorite place to dine or eat out in Ashland is the South Shore Brewery's Deep Water Grille and the LC Wilmarth Tap Room. We were first drawn there because its a home town brewery (South Shore was one of the earliest craft brewers around the lake (established in 1995) and their award-winning Nut Brown Ale. But once we tried the food, we had a double reason to return.

Events, Attractions, and Things to Do and See while
Visiting Ashland Wisconsin.

(see links at the bottom of the page)

There are actually three dining and drinking establishments within the South Shore Brewery complex, located side-by-side and each with their separate street side entrances. The Deep Water Grille is the most formal of the three with the most complete menu. However not so formal that you feel like you can't wear casual clothes.

The Alley Sports Bar, Ashland, Wisconsin

The LC Wilmarth Tap Room is a step-back-in-time to a grand old pub atmosphere. Most of the seating is around the oval-shaped bar with a few tables at either end. Free popcorn is available and you can order food service off either the Deep Water Grille menu or the menu of The Alley, the adjacent sports bar and pizza parlour. On our most recent visit, we had two of the Deep Water sandwich baskets. I had the Cajun Grilled Lake Superior Whitefish Sandwich with Spinach, Tomato, Red Onions & Caper Dill Mayo on a Hoagie Roll. Jo had the Black Angus Burger with Lettuce, Tomato, and Pepper Dill Ranch on a Kaiser Roll plus Swiss Cheese and Mushrooms. We both ordered the house salad, a nice combination of mixed greens and veggies. Both were excellently presented, served hot, and were quite tasty. Jo is a burger connoisseur and felt the Black Angus compared quite well against the best burgers in Duluth (see our reviews) and was priced a little less than those in the "big city." And for me, a Lake Superior Whitefish dinner or sandwich basket is my benchmark. South Shore's gets 4.5 stars from me, just a shade below the Angry Trout's Whitefish in Grand Marais. But you can't top beer fresh from the brewery. I had the Nut Brown Ale, my all time favorite; Jo had the Rhodes Scholar Stout, which compared well to her usual choice and favorite Lake Louie Porter. (Here's South Shore's complete Beer List)

A check of online reviews indicates both the Deep Water Grille and The Alley are popular places and well-liked for food, service, and ambience.

Reviews of Other Ashland Restaurants

Molly Cooper's Lounge, Chequamegon Hotel
We've eaten here a few times and have been pleased with their food and service. What we like best here is the view of the lake and their outdoor deck, best in Ashland. And generally decent beers on tap. But it has been a few years since we dined there and there have been ownership changes in the hotel. Reviews online are generally good for food and ambience, but there have been recent reports of inconsistent service.

Second Street Bistro
We discovered this place a few years ago when were looking for a place within walking distance of Kreher Park Campground. A quaint, intimate place with a more sophisticated menu. Not crowded, upscale dining but formal wear not required. I forget what we had for dinner but remembered it being exceptional and not as pricey as I would have guessed. Our server was friendly and quite polished. Online reviews support the exceptional quality of their cusine, gets rave reviews, and people like the atmosphere of the place - bistro is a good name. They have music on Friday evenings. Only downside was a few people found the service aloof or un-welcoming; they felt like out-of-towners intruding on a local scene. That wasn't our experience, however ours was a few years ago when they were just opening and not as well known.

Buddies Burgers
This is a fun, retro burger and fast food joint. Set up like an old fashioned soda fountain, complete with some great malts, and background music from the 60s and 70s. You half expect LaVerne and Shirley to come bopping in the door any moment. Prices decent and food was good too. Online reviews are generally good. People like the food and the 50s-60s experience. There were a few recent complaints about slow or inattentive service.

Hugos Pizza
Hugos is a fun, busy place with good homemade style, secret sauce pizza, a decent selection of beers, fast service and reasonable prices. They also have other sandwiches, dinners, and a friday fish fry. On our last visit we had some very good Chicago Style pizza in the solarium. Online reviewers give it good reviews for food and service . . . Nothing fancy but great pizza, good service.
4.2 stars average rating on Google.

FreeHands Farm Restaurant
I discovered this place online while doing reviews for this article. Didn't know they existed as it is on the far south side near the airport. The farm also has a full-service greenhouse and its barn and landscaped grounds serve as an event center for weddings and other activities. The restaurant gets rave reviews on Trip Advisor so we've got to add this to our to-do-dining list in Ashland. Plus we are garderners so the greenhouse alone would be worth the visit.

PS The restaurant is seasonal, closed during the winter months. Opens in May