“A Waitress Named Diane,” AKA, The Old Fashioned Bar Crawl

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 and deer head mounted on a wall by a waitress named Diane.

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.

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.

Wait a second… brandy? Olives? Yes, you might think an Old Fashioned is made with whiskey and simple syrup but you would be wrong! A true Old Fashioned, a Wisconsin Old Fashioned, is made with brandy and olives.

If you haven’t tried it, you really should. Check out my recipe so you can make a proper Old Fashioned for yourself.

Now on to the tour!

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 that 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.

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 with 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.

The casino has tons of slots, fun dealers, and unique card games. There is also a golf course that is a favorite of ours as well as a decent resort and newly updated restaurant.

I would also boast that they make one of the best Bloody Mary’s around. Speaking of which, if you’re more of a Bloody Mary person, we also did a Bloody Mary Tour of the Northwoods as well.

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.

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 that’s 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.

It’s got 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!

Next up is 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.

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!

I decided to head 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 featuring bowls of fresh horseradish, pickles, marinated mushrooms and more!

I definitely have Bloody Mary remorse for not partaking in the Bloody Mary Bar but 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 looked mouth-watering and delicious. For all of these reasons, I will be back.

The Redman Supper Club, an old favorite, was another stop. Everything about this place is perfect to me: great drinks, great service, great food, and great atmosphere.

A night out at The Redman is always a treat.

The Old Fashioned is, like everything else, perfection. It’s a perfectly muddled, nice balance of salty and sweet with great ice.  For my family a trip to the Northwoods isn’t complete without a stop here.

If you have a friend or relative who has one of those awesome basements with a great bar that throws the best parties, Brew’s Pub is the Wisconsin Bar equivalent of that friend.

It’s a great sports bar with 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