Underrated: Madison’s Cocktail Scene

Wisconsin is famous for cheese. No qualms there. But did you know it’s also one of the booziest states? In fact, seven of the booziest cities in the U.S. are in Wisconsin. Madison ranks fourth. I recently did some investigating. And by investigating, I mean drinking while traveling. Madison’s cocktail scene is an underrated experience that’s worth a trip to the city all by itself. (Fun fact: A Wisconsin Old Fashioned adds brandy.) 

Below are seven of my favorite places. Plus, a few bonus picks at the end. Cheers. 

Lola’s Hi/Lo Lounge is a cool twist on the HiFi bar. As they put it, Lola’s is a “‘Wisconsin fancy’ Midwestern spin on the HiFi bar. A HiFi love letter to the low brow.” Inspired by Lola’s Tomcat Lounge in Nazianz, WI, Lola’s Hi/Lo Lounge is decorated with Marilyn Monroe memorabilia and vinyl records lining the wall behind the bar, which is soaked in moody red lighting. Lola’s follows the Hi-Fi trend with a quality sound setup and a DJ spinning records. 

From classics like the Sazerac or their seasonal Electrolytes! (Death’s Door gin, Beren’s brandy, Luxardo maraschino, watermelon, tart orange, and Peychaud’s Bitters), their cocktail menu doesn’t disappoint. Plenty of food options, too, but definitely check out their Sichuan chicken dumplings. And, of course, their pizza menu.

Thirsty for a late night cocktail? I was, and bartenders and customers agreed that Nattspil is the place to go. There’s no sign, but it’s not hard to spot the small two story building between two alleys. Nattspil describes itself as a “Chinese Norwegian Pizza Disco,” and the red glow from their paper lantern inspired lights sets the mood. Some nights are also DJ’d. 

I craved an Old Fashioned, so I stopped in for their J. Henry Classic Old Fashioned. The menu includes cocktails stirred and shaken for just about everyone, like their Trinidad Sour, Vesper, White Negroni, or the El Diablo. Balance out those spirits with shu mai dumplings, spicy cheese wontons, three cup chicken, and wood fire pizzas.

Named by Bon Appétit as one of the nine best bars of 2025, Public Parking Bar is where mixology witchcraft comes alive. They are self-described as “a world-class carnival of sophisticated mix-illogical drinking dalliances.” 

Each cocktail’s magic is paired with an equally outlandish name, like “Grandma Hates My Neck Tattoo” (Lost Irish Whisky, Lustou Spanish Brandy, strawberry rhubarb shrub, balsamic vinegar, roasted barely, chicory, dandelion root, honey, and lemon) or “The Suspense is Terrible, I hope It’ll Last” (Toki Japanese Whisky, sake, lemon, yuzu, hojicha coconut cream, shichimi, seaweed). Bartender Jen even showed me the tattoo that inspired the drink. The presentation is as surprising as the drinks themselves. Their “We Met on Ashley Madison” cocktail is served in a red slipper.

Named after Madison’s first mayor, Jairus Fairchild, Chefs and co-owners Itaru Nagano and Andrew Kroeger won the 2023 James Beard Award for Best Chef: Midwest. The elevated atmosphere and hospitality stands out. Their swordfish and Alaska halibut are fantastic, and the Maitake Tempura is addicting and worth every penny. 

The bar at Fairchild is just as much of a culinary experience as its menu. Check out their Chalet Soirée (gin, lime, Peychauds, absinthe, Génépy) or the Tee Time (bourbon, rye, lemon, black tea, Sirene Canto).

Greenbush Bar is an iconic but unassuming and speakeasy-like pizza bar in the basement of the old “Italian Workmen’s Club.” From the entrance, there’s an unmarked door to the left leading to a dining space lit with red, blue, green, and orange string lights and candlelit tables. It’s a comfortable setting and every seat was filled. 

The pizzas looked fantastic and their cocktail menu of spritzes, a mezcal mule, and ginger side car, along with the contextualized drinks like the Door County Jack Rose (Lairds Old Apple Brandy, Door County Cherry Syrup, lemon, and lime) is a nice exploration of mixes. The bar staff was friendly and my Greenbush Old Fashioned with Elijah Craig Small Batch Bourbon hit the spot.  

Open until midnight, Leopold’s Books Bar Caffè is the place to go if you like to hold an espresso or cocktail in one hand and a book in the other. Their books are organized by country of origin and the well-lit atmosphere is friendly for a good (quiet) conversation with friends. 

My visit was quick, but I loved their Oaxacan Negroni (Del Maguey Vida Mezcal, sweet vermouth, Campari, chocolate bitters).

Gib’s Bar is built into a Victorian house in the quirky Willy Street neighborhood. It feels like a place to hang out with friends. Gib’s offers a monthly rotating Community Cocktail, where a portion of the sales go to a cause. They have a nice selection of signature cocktails, like their Nitro Amaretto Sour (Bourbon, pineapple cordial, orange & argan oil) or Batch Please (State Line gin, snap pea juice, thyme, cordial, lemon juice). If you want some pizza to go with that, they are next door to Grampa’s Pizzeria.

Oz by Oz, The Robin Room, The Cardinal Bar. There are three more. Just for good measure. If cocktails are your soft spot, then you’ll fall in love with Madison.