In January, we take the cold plunge into winter. It’s a string of dark, tempestuous days with few seasonal experiences to gather around. This time of year, we’re extra grateful for the hangouts that make weathering January just a little less glum. There are many Madison bars that, for some, feel like an extension of the home living room. It could be the cozy and eclectic spot where you can hide behind a novel while you double-fist an espresso and a glass of wine. Other spots are unassuming dives that let you embrace different sides of your persona on any given night. Will you shrink into the corner this time or perform boldly at the billiards table? And at the neighborhood bar, there’s no need to make plans — just show up and you’ll find familiar faces.
THE COZIEST | Leopold’s Books Bar Caffè
Leopold’s sometimes feels like it could be the personal, eclectic study of someone’s worldly grandfather. It’s the kind of place you walk into and expect to hear the thrum of an upright bass harmonizing with the gentle clinking of coffee mugs and chatter. The bar area and bookstore effortlessly flow together, inviting you to migrate back and forth as many times as your glass needs refilling. Even when you sit down at the mosaic-tiled bar for a nightcap, the faint smell of coffee lingers — that itself seems like a metaphor for cozy. Leopold’s is as cosmopolitan as it is intimate. The aesthetic is anchored by the restored art deco back bar and emanates into a somehow synchronous pairing of dissonant design ideas — tropical wallpaper peppered with exotic birds, a red banquet booth and marble tables, potted birds of paradise and a painted portrait of the owner atop the bar, plus a very mod book nook. Drift into Leopold’s on any snowy day and let the books organized by country take you on many whirlwind vacations. Warm up with a Dale’s Cappuccino Boom Boom, a cappuccino cocktail spiked with Grand Marnier, amaretto and Bailey’s, and settle in with your newest read and an old-school periodical. And if you happen to be there on a Wednesday evening, let the live jazz band provide the soundtrack to the snowflakes falling outside. 1301 Regent St., leopoldsmadison.com
NEIGHBORHOOD FAVORITE | The Village Bar
It makes sense that a neighborhood with a tightknit community would also have an esteemed gathering spot. One small enough that it feels a bit crowded at any time of day — not the kind of crowded that turns you away at the door, but the kind that invites you to pack in. Everyone gathers around one TV to create a singular, ecstatic moment when the Badgers sink a free throw in double overtime to win the game, or the Packers reclaim the lead after giving up 21 points in the third quarter. The Village Bar is that place in the Westmorland neighborhood on Madison’s near westside. Its wood-lined, knickknacked walls and ceiling, old-timey letter board menu, behind-the-bar kitchen and friendly bartenders are so treasured that The Village Bar has its own history booklet compiled by the Westmorland History Committee. And its renowned burger is so good that legendary comedian Jerry Seinfeld arrived in a limo just to taste it. In a snowstorm, “Villagers,” as patrons are affectionately called, don’t have to venture far to escape the onslaught. In fact, it barely feels like being snowed in when half the neighborhood is at the bar. 3801 Mineral Point Road, Facebook: The Village Bar
DIVIEST DIVE | The Crystal Corner Bar
It’s brutally cold out. Williamson Street is barren and nearly quiet, but you keep trekking the snow-caked, seemingly endless pavement. Then, all of sudden, the hearty glow of red and green through frosted glass comes into view. The Pabst Blue Ribbon sign hangs above the flaming light like a beacon — it’s The Crystal Corner Bar welcoming you inside. Step through the door and level your expectations. There are pinball machines and dart boards, three glowing green pool tables and an oval bar unmoored through the middle of the joint. Bare-bones black leather bar stools sit around the counter, with a popcorn ceiling, a molding of late ’80s hotel wallpaper, rows and rows of autographed portraits from visiting musicians and a glass case of trophies won in city sports leagues rounding out the decor. The Crystal Corner doesn’t try to be anything but a neighborhood dive bar — especially now, after navigating the business through COVID-19. But there are still plenty of reasons this spot has a committed following beyond being a safe haven on a chilly night. The drinks are cheap and strong, and live music is a staple. If nothing else, it’s a reliable spot to shoot the breeze over a few beers and a round of pool. 1302 Williamson St., thecrystalcornerbar.com
For more hometown favorites, go to…
Mickey’s Tavern for the red-hued ambiance. 1524 Williamson St.
Bristled Boar Saloon & Grill for a game of billiards in a backwoods setting. 2611 Branch St., Middleton
Genna’s Lounge for an Insta-worthy cocktail photo in a lowball glass. 105 W. Main St.
Blue Moon Bar & Grill for a pinball battle with the besties. 2535 University Ave.
The Mason Lounge for a Falbo Bros pizza with your craft beer. 416 S. Park St.
Main Depot for a game day Jell-O shot. 627 W. Main St.
Silver Dollar Tavern for a classic wood-paneled dive experience that’s cash-only. 117 W. Mifflin St.
Great Dane Pub & Brewing Co. for a shuffleboard match during the big game. 123 E. Doty St. (downtown)
Come Back In to show off your pipes at open mic night. 508 E. Wilson St.
The Ideal Bar for jukebox tunes and Pabsts. 1968 Atwood Ave.
The Malt House for an unplugged evening (no TVs). 2609 E. Washington Ave.
Prost! for a two-liter boot. 401 E. Washington Ave.
The Harmony Bar for live music and a famous walnut burger. 2201 Atwood Ave.
Echo Tap and Grill for competitive trivia on Thursdays and Sundays. 554 W. Main St.
Paul’s Club for an adorable meet-cute moment under the tree. 204 State St.
Le Tigre Lounge for a sensual staring contest with a tiger. 1328 S. Midvale Blvd.
Tip Top Tavern for a cozy meal at a friendly bar. 601 North St.
Choose Your Own Adventure
There’s a bar for every activity: EAT at Paradise Lounge. Order the famous Paradise Burger in this well-loved dive off the Square. 119 W. Main St. | READ at The Library Café & Bar. Looking for another fun spot to hide a hot toddy behind a book? Try The Library. (wink, wink) 320 N. Randall Ave. | PLAY at The Weary Traveler Freehouse. Looking for some slow fun? Dust off a board game from the shelf at The Weary. 1201 Williamson St. | PEOPLE-WATCH at The Plaza Tavern. Settle into a booth at Plaza and wait for some of Madison’s best (and funkiest) dressed to file in for Thursday’s Long Island Night. 319 N. Henry St. l CHAT at Gib’s. This bar spans two stories of a Victorian house and feels like one big living room with nooks and crannies for intimate conversations over drinks. 1380 Williamson St. | SING at Ohio Tavern. Start brainstorming a crowd-pleasing song — The Ohio hosts karaoke every Saturday at 9 p.m. 224 Ohio Ave.
READ MORE | Madison BarsAs Seen On TV: We’ve imagined the equivalents of some iconic pop culture bars right here in Madison. Some are loosely connected, and others are spot on. It’s fun to think that we can experience the world like some of our favorite characters — even for just one night.
Emma Waldinger is associate editor at Madison Magazine.
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