A Waitress Named Diane ….

September 3, 2017thetipsyhousewife

Travel Wisconsin ran a commercial a few years back about the Wisconsin Supper Club and The Old Fashioned Cocktail. In the commercial it teaches that an Old Fashioned is served in a ten ounce glass, with a maraschino cherry, and an orange slice but that a REAL Old Fashioned must be served in a room with a brick fireplace, an a deer head mounted on a wall, by a waitress named Diane.  (See the commercial here The Wisconsin Supper Club) As a lover of the Wisconsin Supper Club scene and pretty much all things Wisconsin, this commercial gives me all the feels.  From all of this, the idea of my Old Fashioned Cocktail Crawl was born. I began to plan my old Fashioned Cocktail Tour. My plan was to stop at  some old favorites, and to venture out to some new ones.  I decided on ten locations, and at each one I would order the Old Fashioned exactly the same, Brandy, Sweet with Olives for consistency.

My first stop was in Conover, Wisconsin at Lanny’s Fireside. Lanny’s is a more upscale Northwoods restaurant, with white tablecloths and a cozy bar. One of my favorite parts of this place was the delicious horseradish cheese spread and crackers they had out for everyone to enjoy. The bartender was clearly a cocktail expert.  He muddled up my Old Fashioned perfectly, nutty and sweet. He also whipped up a Grasshopper Cocktail for my drinking partner that was an ice cream delight. The cool thing about Lanny’s is across Highway 45, there is a water show called the Chain Skimmers Water Ski Show.  It is a group of young locals who perform a ski show for the crowd on a small lake. It’s a must see.  This was my first time at Lanny’s and I am excited to go back to eat and sit at the great bar filled with friendly locals.

Lanny’s Fireside ~ Conover, WI

My next stop was at Northern Waters Casino Resort.  This place is an old favorite of ours.  It was recently remodeled and the bar area was updated to a lively sports bar The Old Fashioned offering was solid, plenty of ice, a great Brandy and the perfect amount of sweet. If you are ever in the area, they have a great snack bar that is a favorite of ours. Tons of slots, fun dealers, and unique card games.  There is also a golf course that is a favorite of ours as well. There’s also a decent resort and newly updated restaurant.  I would also boast that they make one of the Best Bloody Mary’s around.

Northern Waters Resort ~ Watersmeet, MI

Next up,  Buckshots Saloon and Eatery.  This was also a “new to me” place.  The wait was long, but the Old Fashioned’s were so good I didn’t mind waiting while having two, ok maybe three, of these perfectly crafted drinks.  Buckshots also served up an incredible cheeseburger and the place had a fun and lively vibe.  If I had to pick just one Old Fashioned as my favorite, this one would surely be a contender, every component was on point from the bitters to the sugar.

Buckshots Saloon ~ Eagle River, WI

A classic Lodge here in the Northwoods that is an old favorite of mine is The Gateway Lodge. The Gateway is a local treasure. It is almost a century old and sits right on the border of Wisconsin & Michigan.  They have so many interesting amenities like trap shooting, a gun club, a redwood sauna, a small airport, and a  golf course across the street thats half in Wisconsin and half in Michigan. The historical pictures that adorn the hallways are fun to look at and they have a gorgeous dining room and bar area.  I try to make a stop at The Gateway Lodge every time I am up here.  The bar is one of my very favorites.  Classic charm, cozy booths, even door bells built into the booths that you can ring when you need a refill!  The Old Fashioned was very good here, but the real treat was watching the bartender prepare it.  His muddling technique was a show in itself.  In fact, while he was preparing my cocktails, a local at the bar told me that the bartender is known as the “Love Muddler”  Clearly a title he earned!

The Gateway Lodge ~ Land O Lakes, WI

Rogers Bar in Watersmeet, MI.  Rogers Bar is a small snowmobile bar that is a fun stop for some solid food and great drinks.  The Old Fashioned here was on point.  Classically prepared and went down easy for sure!  If you’re up here riding the ATV & Snowmobile trails Roger’s Bar is a must.

Roger’s Bar ~ Watersmeet, MI

One of our favorite past times in the Northwoods in the Winter is to go bowling.  Our favorite bowling alley was recently remodeled and given new life.  The Alley Lanes & Tavern in Land O Lakes is a fun stop for anyone.  Kids can bowl or play in the video game room, while parents enjoy a drink at the bar. The bar is filled with a great mix of locals, and seasonal visitors.  There is, pool, darts, bowling, and some snacks like chips, pub pizza and pizza fries.  The Old Fashioned here was mixed up by the bartender Chad, and if this were a contest, he would definitely be a contender for “Best Old Fashioned” in the Northwoods.  This Old Fashioned was almost TOO good.  My other favorite thing at The Alley, is their frozen blackberry brandy shots.  The Alley really knows how to show everyone of all ages a good time!

The Alley Lanes ~ Land O Lakes, WI

I headed over to Broken Arrow Bar & Grill in Conover, WI, another “new to me” spot. What intrigued me when I walked in was their comprehensive Bloody Mary Bar.  Bowls of fresh horseradish, pickles, marinated mushrooms and more!  I definitely have Bloody Mary remorse for not partaking in the Bloody Mary Bar, the Old Fashioned made up for it.  The key to a great Old Fashioned is a good rocks glass and Broken Arrow had it going on.  I didn’t eat here but the food that was going past me was mouth-watering and delicious.  For all of these reasons, I will be back.

Broken Arrow ~ Conover, WI

An old favorite, The Redman Supper Club was another stop.  Everything about this place is perfect to me. Great drinks, great service, great food, great atmosphere. A night out at The Redman is always a treat.  The Old Fashioned is like everything else, perfection.  Perfectly muddled, nice balance of salty and sweet, great ice.  For my family, a trip to the Northwoods isn’t complete without a stop here.

The Redman Supper Club ~ Land O Lakes, WI

If you have a friend or relative who has one of those awesome basements, with a great bar, and throw the best parties, Brew’s Pub is the Wisconsin Bar, equivalent of that friend.  Great sports bar, incredible food, a fabulous beer selection and perfectly crafted cocktails.  The Old Fashioned here is one of my favorites because of their great ice to alcohol ratio.  I enjoyed at least three of these when I was here. Two thumbs up for sure.

Brew’s Pub ~ Land O Lakes, WI

This Old Fashioned Tour was a fun foray into Wisconsin Culture.  I enjoyed visiting old favorites and finding a couple of new ones.  I encourage everyone to visit Wisconsin for the Old Fashioned Cocktails, the local flair and the nostalgia of the Wisconsin Supper Club, while you’re there, don’t forget to ask for Diane.

For more about the Northwoods Dining Experience, check out a separate blog post about food of the Northwoods.

Why Foodies Need To Visit The Northwoods 

To Make Your Own Old Fashioned Cocktail, Check Out This Recipe!

The Old Fashioned Cocktail


  • Adeline Skokal

    September 3, 2017 at 8:48 pm

    I enjoy reading your blog feel like I just went on a trip not fond of old fashions I prefer martinis but in a pinch any alcohol will do tnx April

    Sent from my iPhone


    1. thetipsyhousewife

      September 3, 2017 at 8:50 pm

      Thanks so much!

  • Chrissy

    September 4, 2017 at 1:48 pm

    I lived in that area for over a decade, still go up to visit my parents every year, so I’m pretty much familiar with every place on this list. I also know Chad! Very nicely written, makes me feel a little homesick though!

    1. thetipsyhousewife

      September 4, 2017 at 1:49 pm

      I hate when I’m not up here so I totally understand how you feel! Thank you so much for reading! I am the new food columnist for the Border Bulletin too!

  • John Leigh

    September 7, 2017 at 11:29 pm

    Just last year we lost a family owned property that was around 100 years old where I had going for more than 65 years. We know all of those places , but would also definitely suggest Club 45 just North of Conover on “Old 45” road.

    1. thetipsyhousewife

      September 7, 2017 at 11:37 pm

      I’m sorry to hear you lost your place. I’m sure it was great. I know Club 45 well. I will definitely be making a stop there on my next food/drink tour. Thank you so much for reading my blog post!

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