Ashland locals or frequent visitors know and love this staple of the Ashland dining scene, located on Ashland’s historic Main Street. This place has a classy atmosphere that welcomes folks of all cravings and favorites. With three incredible establishments in one, this joint is none other than the Deep Water Grille, adjacent to The Alley, and South Shore Brewery.
These three establishments coexist in deliciousness, nestled into the historic L.C. Willmarth building which is located in downtown Ashland.
There’s a variety of dining experiences and restaurants in Ashland Wisconsin to indulge in while you’re soaking up the lake life on Lake Superior, and if you’re searching for a family-friendly restaurant that doesn’t miss out on deliciousness and cold brews, you’ve hit the jackpot!
With a well-rounded menu, fantastic beer options, a dazzling kid’s menu, and vegetarian options, no matter what your dining group looks like, everyone can find something to enjoy at Deep Water Grille.
Where is Deep Water Grille?
You can find Deep Water Grille, The Alley, and South Shore Brewery right on the historic Main Street of Ashland!
Get into the lake life bustle of Ashland by exploring the downtown streets, wonderful bookstores, and where other fantastic establishments, such as Black Cat Coffee, are just a quick walk away!
808 Main St W, Ashland, WI 54806
What’s on the Menu at Deep Water Grille
From Starters to Entrees, there are plenty of mouthwatering options to sink your teeth into at Deep Water Grille, and all at fairly reasonable prices!
Photo credit: J Chapiewsky (CC)
Below is a broad list of items that Deep Water Grille currently offers. Sides aren’t included below, but contain traditional sides such as a variety of fry choices, house salads, soup, fresh fruit, and coleslaw. For further ingredients and pricing details, please take a look at their online menu.
Starters
- Spinach Artichoke Dip
- Chicken Wings
- Nachos
- Garlic Shrimp Dip
- Chorizo Stuffed Mushrooms
- Sesame Soy Steak Tacos
- Wisconsin Cheese Curds
Salads
- Thai Sweet Chile Salmon
- Roasted Garlic Pesto Caesar
- Bay City Cobb
- Garden Salad
- Northwoods
Soups
- Nut Brown Ale Beer Cheese
- Chicken Wild Rice & Mushroom
- Soup Du Jour
Sandwiches
- Grilled Chicken Breast
- Black Angus Burger
- Grilled Smoked Ham & Cheese
- Lake Superior Whitefish Sandwich
- Reuben
- Smoked Turkey Wrap
- Smoked Pulled Pork
- Sandwich and Cup of Soup
Entrees (All Day)
- Nut Brown BBQ Smoked Pork Ribs
- Lake Superior Whitefish
- Fettucine Alfredo
- Broiled Jumbo Tiger Shrimp
- Honey Garlic Glazed Salmon
- Jerk Chicken
- Jambalaya
Entrees (After 4:30 PM)
- Parmesan Breaded Pork Loin
- Bleu Cheese Crusted New York Strip
- Shrimp Mac & Cheese
- Pan Fried Pork Loin
- Orange Chicken
- Smoked Ribeye
The Alley Menu Overlook
Moving on over to The Alley’s menu, adjacent to Deep Water Grille and South Shore Brewery, you can expect a delicious classic Brewpub experience! From the brewtastic food choices to the timeless atmosphere, your tastebuds are in for a prime Wisconsin time.
Below is a broad list of The Alley’s menu items. For a more detailed look at their prices and ingredients, please take a look at their online menu.
Featured Items
- Fried Pickles
- Garlic Shrimp Dip
- Reuben Pizza
- Poutine
- Curd Burglar
Starters
- Jalapeno Cheese Curds
- Beer Battered Onion Rings
- Pretzel Sticks
- Beast Fries
- Elote Dip
- Beer Battered Perch Tacos
- Parmesan Truffle Fries
- Spinach Artichoke Dip
Soup
- Nut Brown Ale Beer Cheese
- Cream of Chicken with Wild Rice & Mushrooms
- Soup du Jour
Wings/Sauce/Dry Rub
- Traditional or Boneless Wings
- Buffalo (Sauce)
- Sweet Chili (Sauce)
- Nut Brown BBQ (Sauce)
- Bourbon (Sauce)
- Honey Sriracha (Sauce)
- Thai BBQ (Sauce)
- Garlic Parmesan (Sauce)
- Peanut Butter & Jelly (Sauce)
- Asian BBQ (Sauce)
- Honey Mustard (Sauce)
- Jamaican Jerk (Sauce)
- Cajun (Dry Rub)
- Ranch (Dry Rub)
- Chipotle BBQ (Dry Rub)
Burgers
- Alley Angus Burger
- Wisco Frisco Burger
- Mean Black Bean Burger
- Turkey Wrap
- Bar Burger
- Brew House Burger
- Chequamegon Chicken
- Goober Burger
Sides
- Waffle Fries
- Sweet Potato Fries
- Straight Cut Fries
- Cup of Soup
- Side Salad
- Fresh Fruit
Salads
- Thai Sweet Chili Salmon
- Roasted Garlic Pesto Caesar
- House Garden Salad
- Northwoods
- Bay City Cobb
Brick Oven Pizza (Build Your Own Pizza Options Available)
- Margarita
- The Works
- Madeline Island
- East Ender
- The Three Meat
- Big Bay Bacon Cheeseburger
- Four Cheese
- Asian BBQ Chicken
Entrees (After 4 PM)
- Steak Frites
- Beer Battered Perch Fish Fry
- Grilled Sweet Chili Salmon
Cast Iron Mac & Cheese
- Six Cheese
- Big Popper
- Chicken Bacon Ranch
- Buffalo Chicken
- Asian BBQ Chicken
- The Cook Out
Specialty Drinks
- Banana Old Fashion
- Blackberry Fizz
- Island Martini
Kid’s Menu Options
Who said kiddos aren’t little foodies themselves? There’s something for every kid, from the picky eaters to the adventurous triers on this Kid’s Menu!
Below is a broad overview of the Kid’s Menu. For prices, please take a look at their online menu.
- Fruit, Cheese, & Meat Plate
- Grilled Cheese with Fries
- Hamburger with Fries
- Cheeseburger with Fries
- Chicken Strips with Fries
- Mac & Cheese with Fries
- Whitefish (Deep-fried or Broiled) with Fries
- Corn Dog with Fries
South Shore Brewery
Also in the mix of Deep Water Grille and The Alley is the cold and the brewtiful South Shore Brewery, which has been a part of the on Lake Superior area since 1995. Currently, the Pilot Brewery and Main Office are located in Ashland, right next to Deep Water Grille, and their Production Brewery & Taphouse is located in Washburn, WI.
“The Deep Water Grille and The Alley are both located in the historic L.C. Willmarth downtown building along with our pilot brewery. They do the food, we do the beer. Both restaurants have an enjoyable atmosphere, unique and creative cuisine for all appetites, and menu choices that creatively use our beers: Beer Cheese Soup (Nut Brown Ale), Pale Ale Onion Soup, Braised Onions and Poultry Marinade (Pale Ale), and our homemade Apple BBQ sauce.”
– South Shore Brewery Website
It’s all part of the dining experience to be in the same building as a dedicated Wisconsin brewery that’s crafting deliciousness while you’re enjoying a scrumptious meal yourself! You can take a look at their current beer variety on their website and stop in person to check out what’s on Tap!
Praise & Hype for Deep Water Grille
It’s always reassuring and inspiring to hear others’ experiences in uncharted territory, especially when it comes to something as sacred as food! Here’s the buzz on Deep Water Grille to get you revved up for your future dinner plans.
“This bar was highly recommended by the locals, and we discovered why.
Our bartender ‘Mike’ was fantastic, and was an excellent conversationalist.
The food was amazing!
I ordered a grilled chicken sandwich that was absolutely delicious. I overheard other patrons discussing how good their food was as well.The drinks were made perfectly.
The bar is constructed of salvaged pieces from a bar that was demolished. The entire place felt rustic and comforting.
The Deep Water Grill is adjacent to the Alley restaurant, and has something for everyone.”
– T. K ⭐⭐⭐⭐⭐
“Loved it, went there for my birthday dinner! Service was great! Food was very good, proportions were filling! Starters we had the stuffed mushrooms, we cleaned the plate! Had the grilled salmon salad, yum! Partner had meatloaf, again very good! Definitely will stop in again!”
– Barabra K ⭐⭐⭐⭐⭐
“Excellent restaurant in all aspects! Food was great at a great price point. All with the best, friendliest service I could ever hope for. Every detail of the food was exceptional. The Lake Superior whitefish prepared perfectly, the mac n cheese best ever, and even the mashed potatoes were mind blowing.”
– Michael B ⭐⭐⭐⭐⭐
“We had 3 different meals & they were all delicious! Butterfly grilled shrimp, glazed salmon & Cajun whitefish all with wild rice & fresh steamed vegetables & grilled asparagus with the salmon. We also had beer cheese soup that was not too rich & very good. We shared the chocolate lava cake-fabulous! Our service was exceptional with Jonathan our server.
– Judy S ⭐⭐⭐⭐⭐
We loved the décor & atmosphere in this older building! Very relaxing!”
Is anyone else’s stomach growling for some brewpub goodness after reading all of those delicious food options? Talk about a pub foodie haven!
Food is a key ingredient in creating a long-lasting memory with those you love. When you make a reservation at Deep Water Grille, you can look forward to gathering around a dinner table in a timeless environment, surrounded by aromas of buttery and savory goodness.
From all of us here at On Lake Superior, we hope you enjoy your lake life experience and have a memorable and tasty time. Be sure to share all about it on our Facebook Community to keep the Lake Superior love thriving and jiving!
