The best bars & nightlife in Baraboo

“2,000-seat performance venue showcasing national musicians, comedians & family shows.”

“Relaxed tavern in the Kalahari Resort featuring American fare, brews & multiple TVs for sports fans.”

“Prime rib, seafood, burgers & other American meals in an unpretentious setting with a bar & patio.”

“Casual lakeside spot with indoor/outdoor seating, plus burgers, seafood bites & specialty cocktails.”

“Cambridge Winery - Madison Tasting Room pours premium wines from Wisconsin and beyond, plus a lineup of shareable small plates that make lingering easy. A low-key Janesville escape for tastings, catch-ups, or checking their events calendar when you want something mellow, grown-up, and quietly delightful.”

From the Madison newsletter, September 13, 2026

“FIVE Nightclub has kept the party loud and welcoming since 1998, with a big dance floor, DJs, and a weekly calendar that actually delivers: drag queen bingo, karaoke, Latin Night, RPDR viewings, line dancing, and the Mad City Drag Revue. Show up, find your people, stay for another song.”

From the Madison newsletter, September 14, 2026

“Badger Tavern keeps the traditional Wisconsin tavern vibe alive with a come-as-you-are feel, cold drinks, and bar-and-grill comfort that hits when you want something familiar and satisfying. Neighborhood-y in the best way, it’s the kind of spot you wander into once and somehow end up on a first-name basis.”

“Plain Spoke Cocktail Company is an easy-going tasting room where cocktails feel like home. Expect fresh, balanced, never pretentious pours like a Brandy Old Fashioned, Passion Fruit Margarita, or Bourbon Smash, plus canned cocktails for your fridge... all set to hip tunes and friendly chatter.”

From the Madison newsletter, September 7, 2026

“Tailer Nicole Wine and Cupcakes Lounge pairs curated flights of Pinot to Prosecco with cupcakes like Red Velvet and Rosé Berry, plus staff-guided pairings that actually make sense. Swing in for Wine Mimosa Saturdays, sip-and-paint nights, or book a private celebration... because Tuesday deserves dessert.”

From the Madison newsletter, September 5, 2026

“Need a brainy night out that still comes with a pint? Minocqua Brewing Company | Madison Taproom turns its “Home Away From Home” into a lively hub with live music, remote radio, poetry, stand up, and thoughtful talks in science, politics, and architecture, plus their Progressive Beer and more.”

From the Madison newsletter, September 6, 2026

“Karben4 Brewing is that warehouselike taproom pouring house-brewed, malt-forward ales alongside a legit lineup of sandwiches, salads, and sides.”

From the Sun Prairie newsletter, August 31, 2026

“Stylish venue with a creative cocktail menu showcasing old classics and the bartenders' creations, and serving sushi.”

“ALT Brew is Madison’s 100% gluten-free brewery, turning alternative grains into legit IPAs, crisp lagers, and seasonals that don’t taste like a workaround. If beer usually hates you, this nearby spot loves you... and even your pickiest hophead neighbor will admit it.”

From the Madison newsletter, August 28, 2026

“Inventive craft cocktails & unique snacks offered in a snug two-story house with vintage decor.”

“Tucked beneath the Italian Workmen’s Club, Greenbush Bar has been serving iconic tavern style pizza since 1993, with a backbar built for lingering. Swing by this week for iconic tavern style pies, a lively pop-up piano bar, or the monthly Italian Disco, and soak up true Greenbush neighborhood history.”

From the Madison newsletter, August 17, 2026

“Family-owned since 1964, Genna's Lounge is the Capitol Square staple housed in a landmark Gothic Revival flatiron, pouring classic cocktails, a Bloody Mary bar after the farmers’ market, and prime patio lounging when it’s warm, with cozy upstairs hangs when it’s not.”

From the Madison newsletter, August 4, 2026

“Casual cocktail bar in pared-down quarters features a big whiskey menu & rotating craft taps.”

“Bar & grill with a retro vibe with a big craft beer list including house brews & an outdoor patio.”

“Need an easy win this week, hit The Great Dane Pub & Brewing Company for house-brewed beers that actually taste like someone cares, a menu that swings from brunch to comfort-food classics, and plenty of room to gather the crew or snag to-go platters for game night.”

From the Madison newsletter, August 12, 2026

“Longtime Madison staple State Street Brats keeps it simple and perfect with legendary red and white bratwursts on German buns, squeaky fried curds, and liter steins, plus TVs and a front patio for game days. Easy pick when Janesville friends rally for a UW watch party.”

From the Madison newsletter, August 31, 2026

“Laid-back, modern restaurant serving brisket and pulled pork, alongside mac and cheese, burgers and local brews.”

“Table Wine is a neighborhood wine shop and cozy wine bar in Madison’s Schenk-Atwood that nails the sweet spot between curated and approachable. Grab a glass in the front window for A+ people watching, explore thoughtful picks across wine, spirits, and beer, or join a class, tasting, or wine club.”

From the Sun Prairie newsletter, September 5, 2026

“Restoration Cider makes refreshing, no-nonsense cider, then quietly sends 5% to stream restoration so your midweek pour helps keep our waters happy. Easy-drinking and fridge-friendly, it’s the kind of bottle that turns Tuesday into a tiny win.”

From the Madison newsletter, August 15, 2026

“Sleek spot with floor-to-ceiling windows & dramatic Capitol views for tapas, craft cocktails & wine.”

“Wisconsin-themed, retro-style tavern offering beers, brats & cheese curds (all sourced in-state).”

“Hip, cozy hangout for cocktails, beer & wine served in a wood-accented space with retro fixtures.”

“Stylish cocktail bar with a hidden, cozy feel, craft margaritas and beer, plus a friendly vibe.”

“Boasting 15+ draft microbrews, this snug gathering place offers a mellow vibe & a long whiskey list.”

“Slide into Blue Jack in the One Social District for a chic, intimate cocktail lounge experience with speakeasy vibes, craft cocktails, plus appetizers and dessert to finish. Perfect for a low-key date or friend catch-up, and a solid excuse to upgrade your usual nightcap this week.”

From the Madison newsletter, August 25, 2026

“Cozy hangout with a vintage feel dishing up traditional eats such as grilled cheese & burgers.”

“Comfortable brewpub with outdoor seating, a big beer selection & artful menu of burgers & bar bites.”

“I/O Arcade Bar is the open, inclusive hangout where craft beers, custom cocktails, THC drinks, and mocktails meet more than 70 arcade and pinball machines. Grab a board game, chase a high score on Killer Queen or NBA Jam, then stick around for Kar-I/O-ke Sundays or trivia Tuesdays... perfect reset button for the week.”

From the Madison newsletter, August 29, 2026

“Hip bistro with creative French fare & a lively bar in a former warehouse with Lake Monona views.”

“Industrial-chic gastropub & liquor store serving farm-to-table New American fare & craft cocktails.”