Even though it’s already snowed a couple times, the daylight hours have dwindled significantly, and the Packers regular season is almost over, it’s still technically fall. Yes, the season most of us dread officially begins tomorrow. Though winter’s arrival officially ushers in a cold, harsh, and emotionally-testing period of inactivity that lasts until mid-March, Milwaukee has made sure to combat the seasonal doldrums with a ton of great shows in recent years.
The city will once again be abuzz with a steady helping of top-tier touring comedians and bands, stacked local shows, and even a festival or two thrown in for flavor. If the prospect of another Wisconsin winter has you down in the dumps, here are 24 standout events that might help warm your spirit.
Friday, December 27
Buena Cara (album release) + Pommer, Versio Curs, Known Moons, NATL PARK SRVC
Milwaukee’s own Buena Cara will celebrate the release of its new self-titled album with a Cactus Club show that also features support from Known Moons, Chicago’s Pommer, and a rare outing by Versio Curs.
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.
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.
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.
Friday, January 31 and Saturday, 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.
Saturday, February 1
Mitten Fest @ Burnhearts
After a one-year relocation to Boone & Crockett in 2024, Mitten Fest will return to its rightful home outside of Burnhearts in Bay View. The lineup hasn’t been released yet, but save the date for a full day of live music, rare beer releases, local food and retail vendors, and charity.
Thursday, February 6
Tyler, The Creator + Lil Yachty, Paris Texas @ Fiserv Forum
Less than six months removed from the release of his acclaimed new album, CHROMAKOPIA, Tyler, The Creator will take the stage in Milwaukee for the first time in close to seven years. Lil Yachty and Paris Texas (the rapper, not the former Milwaukee indie band) will kick off this Fiserv Forum affair.
Friday, February 7 and Saturday, February 8
Sean Patton @ The Laughing Tap
Comedian Sean Patton has performed on network television talk shows, been a frequent fixture on Comedy Central stand-up showcases (including his own half-hour), released a few outstanding comedy albums, and has likely been a memorable guest on some of your favorite podcasts. He’s also an actor who has a recurring role on the great new FX series, English Teacher. Now a certified Milwaukee regular thanks to the fine folks at Milwaukee Comedy booking him in recent years, he’ll come to the Milwaukee Comedy-owned and -operated Laughing Tap in Walker’s Point for a total of four shows spread over the course of two nights.
Friday, February 14 through Sunday, February 16
Natasha Leggero @ Milwaukee Improv
Actor, podcaster, accomplished comedian, and Rockford native Natasha Leggero will return to her native Midwest for a total of five Milwaukee Improv performances spread over three Valentine’s Day-adjacent nights. Whether you’re looking to celebrate or flat out avoid V-Day, seeing Natasha Leggero live is an excellent option.
Thursday, February 20
Colter Wall And Friends @ Miller High Life Theatre
The pride of rural Saskatchewan, 29-year-old Colter Wall has both the voice and the material of a much older man. Following 2017’s Milwaukee debut (a sold-out show at The Back Room @ Colectivo) and a Turner Hall sellout in 2019, this continually rising Canadian country star is returning to town with some respected collaborators in tow for a “Colter Wall And Friends” show at Miller High Life Theatre on Thursday, February 20.
Tuesday, February 25
Milwaukee Admirals “Salute To Cowbell Night” with Chris Kattan @ UW-Milwaukee Panther Arena
On Tuesday, February 25, the Admirals will celebrate “Salute To Cowbell Night” at UWM Panther Arena. In honor of the occasion, they’re bringing the guy who had the fourth most lines in the famed “More Cowbell” Saturday Night Live sketch that aired in the year 2000. No, we’re not talking about Chris Parnell or Horatio Sanz. None other than Chris Kattan will “be on hand for laughs, hockey action, and plenty of cowbell!”
Saturday, March 1
The Sloppy Boys Live Podcast @ X-Ray Arcade
What iiiiiiiiiiiiiiis up?! The Sloppy Boys—a hilarious cocktail podcast which features accomplished television actors/writers and members of the party rock band of the same name—will come to X-Ray Arcade for a live podcast recording. What drink of local note will they review? You’ll have to go to Cudahy on Saturday, March 1 to find out!
Tuesday, March 4
Clem Snide @ Shank Hall
Eef Barzelay—the veteran singer-songwriter who releases music under the Clem Snide moniker—makes his way to Shank Hall for a show in recent support of his months-old album, Oh Smokey.
Saturday, March 8
Pom Pom Squad + Caroline Kingsbury @ X-Ray Arcade
About six months removed from the release of the project’s excellent Mirror Starts Moving Without Me, Pom Pom Squad will come to Cudahy to play songs from that new album and other standout songs from its back catalog at X-Ray Arcade. Caroline Kingsbury opens.
Monday, March 10
Faye Webster + Mei Ehara @ Riverside Theater
Following a wildly successful 2024 that included the release of her wonderful album, Underdressed At The Symphony, and numerous appearances at some of the world’s biggest music festivals, Atlanta indie-pop sensation Faye Webster will drop by Milwaukee’s Riverside Theater as part of her “Underdressed At The Symphony” tour. Mei Ehara opens.
Thursday, March 13
Michael Shannon & Jason Narducy And Friends Play R.E.M.’s ‘Fables Of The Reconstruction’ And More + Dave Hill
Famed character actor Michael Shannon and accomplished musician Jason Narducy (Bob Mould Band, Superchunk, Sunny Day Real Estate, and Split Single) will bring their “Michael Shannon & Jason Narducy And Friends” band to Milwaukee’s Turner Hall on Thursday, March 13. The concert, which is the penultimate appearance on a 19-show tour, will celebrate the 40th anniversary of R.E.M.’s sophomore album, Fables Of The Reconstruction. Shannon, Narducy, and company will perform the 1985 album in sequence and in its entirety, along with a few other R.E.M. classics. Dave Hill will open.
Friday, March 14
The Dollyrots + Jinksie, Doubter, Socially Suspect @ Cactus Club
During the band’s 20-plus-year run, The Dollyrots have released more than a dozen albums and EPs, played all over the world, performed with countless punk and rock and roll mainstays, and had their music featured on television shows and in films. Almost exactly a year after playing at X-Ray Arcade, the veteran pop-punkers will come to Cactus Club for a stop on their “Sugar In The Gas Tank Tour” with local support by Jinksie, Doubter, and Socially Suspect.
Martin Lawrence @ Fiserv Forum
Say what you will about Black Knight and the Big Momma’s House trilogy, but Martin Lawrence remains a skilled and influential comedian. With close to 40 years of experience logged on stage and in front of cameras, the transcendent comic still has what it takes to make a massive room of strangers double over with laughter—at least if his Riverside Theater stops in 2011 and 2016 were any indication. The standup legend returns to Milwaukee on March 14 as part of his ongoing “Y’all Know What It Is!” tour.