Not too long ago, Milwaukee in January was pretty much a vacant, blustery tundra that was devoid of entertainment options. Between frigid conditions, uncertainties regarding Packers playoff seeding and the post-holiday hangover, most venues opted to clear their show schedules, while performers—not unlike the rest of us—became hermits, only to emerge for groceries and to use gift cards obtained the previous month. Fortunately, those days are over.
Between a flurry of local festivals, some touring comedians and musicians, and a handful of exceptional local shows, this particular January is especially stacked. Make it your New Year’s resolution to get out more, and use this loaded list of 14 can’t-miss shows as your guide.
Friday, January 3
Mondo Lucha! @ The Cooperage
A few months after yet another Turner Hall sellout, the Mondo Lucha folks will bring the ring to The Cooperage for a more intimate (but equally entertaining) blend of wrestling, burlesque, and music on Friday, January 3.
Saturday, January 4
N/A Day: A “Dry January” Beverage Festival @ The Cooperage
On Saturday, January 4 from noon to 4 p.m., Milwaukee Record will host the fourth annual N/A Day at The Cooperage. The “Dry January Beverage Festival” will give people an opportunity to enjoy unlimited samples of more than 50 products in the wide-ranging, ever-evolving, and rapidly-growing non-alcoholic drink market. WMSE’s own Christreater will DJ the event. The 2025 N/A Day lineup includes non-alcoholic beer and seltzer, kombucha, mocktails, non-alcoholic wine and spirits, craft soda, energy drinks, CBD products, and more. Vendors will range from local operations to nationally-regarded brands. And stick around for the N/A Day After Party at Boone & Crockett from 5-8 p.m.
Holler Home Country & Folk Showcase + Benefit @ Falcon Hall
Some of the city’s best names in the county, folk, and Americana realms will take the stage at Falcon Hall for a fundraising concert that will benefit those impacted by Hurricane Helene. The Holler Home Country & Folk Showcase + Benefit will feature Joseph Huber Band, Old Pup, The Big Heart Kind, King Courteen, Dandy L. Freling, and Bitch Creek. Don Pastor taco truck will also be parked outside Falcon Bowl from 7-10 p.m. and organizers will also be collecting clean hats, gloves, coats, and blankets from Street Angels.
Monday, January 6
Ryley Walker + Michael Vallera @ Cactus Club
Fingerstyle guitar virtuoso and one of the last good Twitter follows Ryley Walker will return to his native Midwest for an early winter tour. The jaunt includes a show at Cactus Club on Monday, January 6. Michael Vallera opens.
Thursday, January 9
Shiner + Fight Dice, Overhand @ X-Ray Arcade
Stop us if you’ve heard this one before: Kansas City rock stalwarts Shiner are coming to Cudahy for a can’t-miss club outing that also features local support by D&D-themed supergroup Fight Dice and the ever-busy Overhand. Originally scheduled to happen December 4, the show will now take place on Thursday, January 9.
Thursday, January 9 through Saturday, January 11
Steve Byrne @ Milwaukee Improv
Steve Byrne has the distinction of being the first comic to ever headline at Milwaukee Improv. Since that run of summer 2021 performances, he’s been a regular visitor to the Brookfield-based club. You can see the veteran comedian, actor, and former star of the TBS series Sullivan & Son at Milwaukee Improv for a total of five shows January 9-11.
Friday, January 10 and Saturday, January 11
Nate Craig @ The Laughing Tap
While he’s now based in Los Angeles, Wisconsin-born comedian/actor Nate Craig returns to his home state with some regularity. In 2023 alone, he opened for Bill Burr at Fiserv Forum in October, headlined a Turner Hall show in November, and helped The Laughing Tap ring in the new year with a NYE-adjacent residency. Craig will come back to Milwaukee January 10-11 to headline a total of four shows at The Laughing Tap.
Saturday, January 11
The Sound Of Kareem City: A Tribute To Twan Mack @ The Cooperage
In November, Milwaukee lost one of its most accomplished and influential hip-hop voices when Twan Mack passed away at the age of 54. Many of Mack’s friends, collaborators, and contemporaries will come together at The Cooperage for a day-long event that will pay tribute to him. “The Sound Of Kareem City” will run from 3 p.m. to close on January 11. Along the way, there will be performances by BLAX, Dame Ellzey, DJ DRiPSweat, King Myles, Rusty P’s, Kamonzi, NilexNile, Spacecrime, and many more. The event is free, but donations and money raised from merch sales will be given to Mack’s mother.
Friday, January 17 and Saturday, January 18
Goblin King Masquerade Ball @ Turner Hall
Awkward Nerd Events will once again transform Turner Hall Ballroom into a magical world of fantasy. There will be themed cocktails and mocktails, a custom curated drag show, photo ops, and more during this two-night event. Formal attire or cosplay is required.
Saturday, January 18
Ben Schwartz & Friends @ Riverside Theater
Fresh off the release of Sonic 3, Ben Schwartz—an accomplished actor, improvisor, and the voice of the speedy blue hedgehog—will come to Milwaukee for what’s sure to be a side-splitting night of improv during his “Ben Schwartz & Friends” show.
Wednesday, January 22
Milwaukee Record presents ‘Teenage Mutant Ninja Turtles II: The Secret Of The Ooze’ @ Avalon Theater
Dudes and dudettes of Milwaukee and beyond: Let it be known that on Wednesday, January 22, Milwaukee Record will be screening Teenage Mutant Ninja Turtles II: The Secret Of The Ooze at Avalon Theater. The action-packed comedy is the follow-up to the original 1990 TMNT. Though it’s decidedly less dark than its predecessor and devoid of known names (excluding the famous Vanilla Ice cameo and a brief appearance by wrestler Kevin Nash in the role of Super Shredder), The Secret Of The Ooze is still a fun, lighthearted, and quotable, box office hit the whole family can enjoy. We hope you go (ninja, go ninja, go!) see it with us.
Friday, January 24
Tigernite + Breakup Tour, Long Line Riders, (D)Vices @ X-Ray Arcade
After years away, Tigernite is reuniting for a great cause. The long-inactive Milwaukee glam rock band will take the “Very Famous” stage at X-Ray Arcade as part of a Planned Parenthood fundraiser. And if a Tigernite show that helps Planned Parenthood isn’t already enough of a reason to go to this, performances by Breakup Tour, Long Line Riders, and D(Vices) make this a can’t-miss affair. There will also be raffles and a Period Product Drive.
Saturday, January 25
4th Annual Bluegrass Winter Heater @ The Cooperage
Though it’s happening in the dead of winter, the Bluegrass Winter Heater will make The Cooperage all warm and toasty with tunes from a phenomenal foursome of great bluegrass bands. The fourth annual affair will feature performances by Valley Fox, Maygen & The Birdwatcher, Joseph Huber, and a headlining set from The MilBillies from—you guessed it!—Milwaukee. Jordan Kroeger (of Chicken Wire Empire) will emcee and Ernest Brusubardis IV (also of Chicken Wire Empire) will be on-site as an “artist at large.”
Friday, January 31 (also February 1)
Lara Beitz @ The Laughing Tap
Milwaukee-born and -raised comedian Lara Beitz (who is now based on Los Angeles) will return to her old stomping grounds January 31 and February 1 to headline a total of three shows at The Laughing Tap in Walker’s Point. In recent years, the homegrown humorist has earned acclaim from Judd Apatow and David Spade, and has become the go-to feature act for the likes of Pete Holmes and Marc Maron.
