Discover the Great Wisconsin Old Fashioned Trail

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If you’re looking for a true Wisconsin tradition, look no further than the Old Fashioned. Whether you choose sweet, sour, or press, this cocktail is a can’t-miss. Come along as we venture across the counties on the great Wisconsin Old Fashioned trail to sip and savor a few all-time favorites.

Vilas County

Start your sip-worthy adventure in Vilas County — the heart of the Northwoods—where The Twilight Supper Club serves up some incredibly famous Old Fashioneds in small-town Land O’ Lakes.

Each cocktail is hand-muddled and the perfect combination of brandy, bitters, and fruit. “The very best in the Northwoods,” a must-try is the Famous Flaming Old Fashioned. Aside from its impeccable flavor, it’s topped off with a mini marshmallow for toasting. And this is just one of the many you can choose from.

Not to mention, this hidden gem offers classic supper club fare to pair perfectly with your cocktail of choice. On the menu is a wide assortment of entrees, plus a massive salad bar. And be sure to save room for an indulgent ice cream drink!

Door County

Continue east to Door County, home to The Mill Supper Club. This go-to spot in Sturgeon Bay serves up a truly legendary Wisconsin Old Fashioned, especially if you’re looking for traditional. Order yours mixed with brandy or bourbon, and choose sweet, sour, or press. Topped off with famous Door County cherries and oranges, this Old Fashioned is a can’t-miss classic. Established in 1930, this supper club continues its tradition of serving great cocktails and food. Here, you can enjoy that traditional supper club fare but with a delicious German flair. 

La Crosse County

To the west, La Crosse County brings its own international flair with La Cave—a French-inspired favorite. Located in La Crosse, La Cave is renowned for its take on the Old Fashioned, especially The Fumé Old Fashioned. And wait until you see the presentation… Settle in for an equally unforgettable meal, starting with the La Cave Charcuterie Board With Cheese and ending with the Vanilla Bean Crème Brûlée. 

Sauk County

Next, head south to Sauk County, which proudly presents Ishnala Supper Club, recognized in Madison Magazine for “Best Old Fashioned” among many other notable titles.

What makes it the best? Click here for a behind-the-scenes look at making the “Best Old Fashioned.” And the Old Fashioned is only the beginning of the Ishnala experience.

Because it’s such a popular spot, the wait can be a few hours—but it’s totally worth it! While you wait, enjoy music on the beach, stroll the scenic path through Mirror Lake State Park, browse the gift shop, and stop by one of the four bars, and eye up the menu—it’s going to be a tough decision! 

Milwaukee County

Last but certainly not least, welcome to Milwaukee County! Our final stop is Central Standard Crafthouse & Kitchen! Here, you sip and savor award-winning cocktails created with Central Standard spirits.

On the list of winners are three out-of-this-world Old Fashioneds—the Classic Old Fashioned, the Wisconsin Old Fashioned, and the Smoked Rosemary Old Fashioned. Central Standard has you covered with good food, too, offering brunch, lunch, and dinner. And you have to top off your meal with Old Fashioned Bread Pudding! 

The great Wisconsin Old Fashioned trail awaits! From Vilas and Door to La Crosse, Sauk, and Milwaukee counties, there are so many incredible Old Fashioneds you simply have to try. So, gather your crew and start planning your sip-worthy adventure across the counties today. 

Hailey Marien, third-generation and granddaughter of Dick Rose, writes for the nation’s longest-running tourism TV show, Discover Wisconsin. Watch the show online at DiscoverWisconsin.com. Follow Discover Wisconsin on Facebook (facebook.com/discoverwisconsin), Instagram (instagram.com/discoverwisconsin), and TikTok (tiktok.com/discoverwisconsin).