Madison Food Guide: Where to find the best old fashioned

The Old Fashioned is a Wisconsin staple. A classic. A cocktail that sings, “I want to party like it’s 1959.”

In Madison, the Old Fashioned is king. We sip them at supper clubs, toast with them at steakhouses, and debate endlessly over the proper garnish (orange slice or cherry — or both?). Also, we pour the good brandy, and occasionally, some new-age bougie bar will pour some good bourbon, and we can pretend to hate it.

So when we asked our readers in Madison to name the best Old Fashioned in town, you stirred up some strong opinions. The results are in, and let’s just say the top three bars are mixing up memories, traditions, a whole lot of brandy, and the occasional hangover.

Here are your picks for Madison’s Best Old Fashioned, with all the fizzy, boozy, bittersweet details you crave.

Cherrywood Smoked Old Fashioned from Northside Lounge – photo by Marissa Haegele

3. Northside Lounge

1022 N Sherman Ave, Madison, WI 53704

Taking third place is a beloved neighborhood joint that’s been quietly killing the Old Fashioned game, including winning the Madison Old Fashioned Week Contest: Northside Lounge. This lovely little retro-style longe proves that you don’t need a fancy zip code or a leather-bound cocktail menu to make a killer Old Fashioned. You just need the right ingredients, a steady hand, and a deep love for the drink — and the community.

Northside keeps their Old Fashioned simple and solid with craft bitters, Korbel brandy, and a handmade orange garnish. They don’t overthink it. Theirs is just a perfectly balanced, nicely chilled, and delightfully drinkable Old Fashioned.

Don’t be intimidated, and come on in. The atmosphere is warm, welcoming, and unpretentious. This is both your grandpa’s kind of bar and your college buddy’s favorite hangout. There’s something for everyone, including mocktails for your sober friends. And don’t forget to check out their community events like holiday parties, themed gatherings, cheese raffles, and more.

2. Tornado Club Steak House

116 South Hamilton Street, Madison, WI, 53703

Sliding into second place is Madison’s favorite Rat-Pack-ish joint Tornado Club Steak House. Tornado isn’t trying to impress you with gimmicks. They impress you with execution. Dim lighting. Leather booths. Servers in crisp black dress shirts. And Old Fashioneds that are pure elegance in a glass.

Tornado’s bartenders are cocktail craftspeople. They take their time, and you can taste it. You can go sweet, sour, or press, but around here, most folks opt for classic sweet — it matches the rich tones of the room and balances out the savory steaks.

If you’re not sure what to order, ask for the barrel-aged brandy Old Fashioned. Tornado keeps a few surprises behind the bar, and this one’s a gem — subtle, smoky, and refined.

Don’t forget that Tornado is, in fact, a steakhouse. Their prime meat is aged, seared, and seasoned like they’ve been doing it for decades (because they have). Try a filet, the rack of lamb, the pork tenderloin, and the escargot, and you won’t be disappointed, but you will be really full.

There’s something about Tornado that feels cinematic (see Rat Pack above). You half expect Sinatra to walk in and order a double while Sammy Davis Jr. croons. It’s moody in the best way, and it’s an amazing spot to celebrate a special occasion.

Their bar is small, intimate, and reservations are strongly encouraged. If you decide to show up to Tornado on a whim, get there early and be prepared to hang out while a table becomes available (with a cocktail in hand, obviously). Considering Tornado Club was one of our readers’ picks for the Best Restaurant in Madison, you know it’s worth the wait.

1. Toby’s Supper Club

3717 S. Dutchmill Rd Madison WI, 53718

This classic Wisconsin supper club offers a heavy pour of nostalgia both in the glass and in the atmosphere. With wood paneling, low lighting, homemade cinnamon rolls, classic cocktail recipes, and the region’s best prime rib, it’s no wonder Toby’s Supper Club won Best Restaurant overall this year as well as the coveted title of Best Old Fashioned in Madison.

This south side legend serves up a brandy Old Fashioned that could make your hardcore Wisconsinite grandpa weep. If you know, you know. Toby’s Old Fashioneds are built the old-school way, hand-mixed with no shortcuts. The result is a balanced, bright, just-boozy-enough glass of self-care that hits every note you want it to. It’s got sweetness, bite, citrus, and warmth.

Ask for your Old Fashioned “sweet with olives.” Sounds weird, but it’s surprisingly amazing. Sweet meets salty in the best way.

Toby’s is a supper club, so you might as well stay for some supper. The Friday fish fry during the season is top-notch. I know I mentioned the prime rib, but it’s worth mentioning twice. But also, Toby’s has a scrumptious “broasted” chicken as well as retro shrimp cocktail and more.

Our readers could have chosen a new, fancy, frilly restaurant with modern touches and trendy plates. But they chose a place where you come for the cocktail and slip back to a different era. You can sip your drink, chat with strangers at the bar, and maybe eat a few pickles while you wait for a warm and filling feast.

READ MORE: The best bar food in Madison, according to our readers