Even though it has already snowed a bunch, it’s been getting dark before 4:30 lately, and the Packers regular season is almost over, winter technically began Sunday. Yes, we’re only on day three of the season most of us dread the most. 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 (check back for our winter festival guide after the holidays!). If the prospect of another Wisconsin winter has you down in the dumps, here are 23 standout events that might help warm your spirit.
Tuesday, December 30
Telethon + Devon Kay & The Solutions, Teenage Ice Age @ X-Ray Arcade
Last November, Milwaukee-born (and now geographically scattered) band Telethon convened at Cactus Club to celebrate the fifth anniversary of Hard Pop. At the end of this month, they’ll get on stage at X-Ray Arcade to give southeast Wisconsin its first live sampling of Suburban Electric, a surprise album the “hard pop” purveyors released back in March. Chicago’s Devon Kay & The Solutions and new local power poppers Teenage Ice Age will precede Telethon.
Friday, January 2
IshDarr + Melotuned, Greyishere, Keeshawn Carter, Lethal Dose @ Falcon Hall
Originally scheduled to take place on November 29, IshDarr’s Falcon Hall show was postponed due to a snowstorm. The accomplished Milwaukee rapper will show he’s worth the wait when he takes the stage at the Riverwest venue on Friday, January 2 alongside the likes of Melotuned, Greyishere, Keeshawn Carter, and Lethal Dose.
Friday, January 9
Field Report @ The Argo
In case you missed the news, Whitefish Bay now has a brand new venue. The Argo won’t just be a stop for touring acts. The establishment will also host an array of lauded local talent, including the always great Field Report, who will perform at the month-old entertainment destination on Friday, January 9.
Friday, January 16
Hey Mercedes + The Hallelujah Ward, Her Head’s On Fire @ X-Ray Arcade
In 2025, Braid headlined WMSE’s Backyard BBQ event. In 2026, Hey Mercedes—a band featuring three of Braid’s members in its ranks that’s already very good—will play its first show in the metro Milwaukee area in well over a decade when they headline a mid-January bill at Cudahy’s X-Ray Arcade. The Hallelujah Ward and Her Head’s On Fire will play in support.
Sunday, January 18
Fortune Feimster @ Riverside Theater
Actor, comedian, and all-around affable person Fortune Feimster is no stranger to Milwaukee, having performed at a past PrideFest installment and working her way up pretty much every rung of the Pabst Theater Group venue ladder through the years. She’ll return to our fair city on Sunday, January 18 to take the Riverside Theater stage as part of her ongoing “Takin’ Care Of Biscuits” tour.
Thursday, January 22
Azthma + DJ Abilities, Kia Rap Princess, Guerrilla Ghost, GetMoses @ X-Ray Arcade
This is just a really good local hip-hop bill that you don’t want to miss.
Friday, January 23
Mondo Lucha! @ The Cooperage
A few months after yet another Turner Hall sellout this past fall, 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 23.
Friday, January 23
Cate Le Bon + Frances Chang @ Vivarium
Welsh singer, songwriter, and producer Cate Le Bon will heat up Vivarium in the dead of winter when she comes to the cozy Milwaukee venue on Friday, January 23 in belated support of her acclaimed 2025 album Michelangelo Dying. Frances Chang opens.
Sunday, January 25
John Mulaney @ Riverside Theater
Writer, actor, Netflix talk show host, and world-renowned comedian John Mulaney is currently at the height of his popularity and his star shows no signs of shrinking anytime soon. See the modern stand up favorite when he comes to Milwaukee’s Riverside Theater on Sunday, January 25 as part of his “Mister Whatever” tour.
Wednesday, January 28
The Toasters + 5 O’Clock Charlie, Local Legends, Meskales @ X-Ray Arcade
The Toasters are nothing short of ska royalty. The constantly touring outfit will stop by Cudahy to head up a midweek show that’s nothing short of a Midwest skanker’s dream, as The Toasters will get oodles of local support from 5 O’Clock Charlie and Local Legends, as well as Madison-based Meskales.
Saturday, January 31
Bone Thugs-N-Harmony @ The Rave/Eagles Club
Oh how the years fly by! Believe it or not, it’s been nearly 30 years since hip-hop legends Bone Thugs-N-Harmony put out E. 1999 Eternal, which featured standout hit “Tha Crossroads.” By this point, that guy in Bone Thugs probably really misses his uncle Charles, y’all.
Saturday, February 7
Wire & Nail @ Ope! Brewing Co.
Since forming back in 2017 on account of its members’ shared love of outlaw country and classic rock, Wire & Nail has crafted timeless tunes that just beg to be played loud while driving around town with your windows down on a warm day. Though the conditions outside likely won’t be conducive to that on February 7, you’ll fortunately be able to see Wire & Nail live in West Allis at Ope! Brewing for free.
Wednesday, February 11
Motion City Soundtrack + Say Anything, Sincere Engineer @ The Rave/Eagles Club
A little more than half a year removed from performing at Summerfest, Motion City Soundtrack will return to their primary Milwaukee haunt—The Rave/Eagles Club—on February 11 as part of a co-headlining tour with fellow emo-adjacent stalwarts Say Anything. Up and coming Chicago pop-punk outfit Sincere Engineer will guarantee you show up early by adding opening support.
Friday, February 13
Chris Fleming @ Pabst Theater
Get ready, Milwaukee. Incomparable comedian Chris Fleming is coming to town on Friday, February 13 to delight, impress, and confuse a Pabst Theater crowd with a night of unconventional material and unmatched physicality. Beyond knowing it’ll be hilarious, we honestly have no idea what to expect from Fleming this time around.
Wednesday, February 18
TOTO @ Riverside Theater
Over the band’s nearly 50-year run (!!!), TOTO has managed some of the most celebrated and enduring soft rock songs of all time, including “Africa” and “Rosanna.” Spend an evening with TOTO on February 18 when the band comes to Riverside Theater as part of an event called, well, “An Evening With TOTO.”
Saturday, February 21
Gin Blossoms (Admirals Postgame Concert) @ UW-Milwaukee Panther Arena
What could be better than going to a Milwaukee Admirals game? Why, seeing Gin Blossoms perform a postgame concert on the ice after the game, of course! That very thing will be happening on Saturday, February 21 and it’s going to be awesome.
Monday, February 23
Nine Inch Nails + Boys Noize @ Fiserv Forum
Like the man said, “Bow down before the one you serve / You’re going to get what you deserve.” And what you deserve is to see Nine Inch Nails live at Fiserv Forum on Monday, February 23. It’s been a minute since Trent Reznor and company made a stop in Milwaukee (like, since 2006?), so this is a can’t-miss show. “Friend and collaborator Boys Noize will join the band again on all upcoming dates,” reads a press release. The show is part of NIN’s “Peel It Back Tour.”
Thursday, February 26
Cosmic Country Showcase @ Cactus Club
Based in Chicago, the Cosmic County Showcase is a musical revue that mixes country-leaning music with elements of comedy, drag, and stunts to create a sprawling and altogether outstanding entertainment spectacle. It’ll return to its home away from home, Milwaukee’s own Cactus Club, for another must-see installment on Thursday, February 26.
Friday, February 27
Steve Martin + Martin Short @ Miller High Life Theatre
Capital L comedy LEGENDS Steve Martin and Martin Short have both managed astounding careers that have spanned decades upon decades, influenced and enthralled generations of fans, and have stood the test of time. Despite all they have done, the duo continues to act together and tour theaters to delight onlookers with their hilarious musings and their charmingly combative friendship. Martin and Short will return to Milwaukee on February 27 as part of their “The Best Of Steve Martin & Martin Short” tour, which will also include performances by Martin’s band The Steep Canyon Rangers as well as Jeff Babko.
Friday, February 27
William Elliott Whitmore + Adeem The Artist @ Shank Hall
What needs to be said about William Elliott Whitmore at this point? Over the course of an impressive career that’s stretched close to 30 years, the Iowa-born folk legend has performed all around the world, shared the stage with an abundance of renowned musicians, and released nine outstanding albums. A frequent Milwaukee visitor, Whitmore will bring his quality catalog and incomparable voice back to the East Side to headline a February 27 show at Shank Hall.
Friday, February 27 and Saturday, February 28
Frank Caliendo @ Milwaukee Improv (three shows!)
Not unlike an American Idol favorite or a late night talk show host, Frank Caliendo’s career is dependent on the work of other, usually more famous, people. As far as this specific comic crevice is concerned, Caliendo is the Kelly Clarkson of celebrity impersonations and the Johnny Carson of pop-culture mimicry. His ability to meld spot-on vocal replications and exaggerated character traits of politicians, actors, and sports figures has yielded the comic such impressive opportunities as a place in the MADtv cast, the role of resident funny man for two football pregame shows, a short-lived TBS show called Frank TV, and the ability to tour the country. He’ll return to his native region February 27-28 for a total three shows at Milwaukee Improv in nearby Brookfield.
Tuesday, March 3
Bridget Everett @ Pabst Theater
In 2013, Bridget Everett straight up stole the show with her raunchy cabaret act when she opened for Amy Schumer at Pabst Theater. Since then, she’s starred in an Off Broadway show she created, was the lead in the exceptional Peabody-winning HBO series Somebody Somewhere, and earned the opportunity to headline shows in many of the same theaters where she used to appear in support of other comics. On Tuesday, March 3, Pabst Theater will get another sex-positive and uproariously funny musical performance from Everett when she brings her “Big Titties.” and “Big Dreams.” to Milwaukee.
Saturday, March 14
Ratboys + Florry @ Vivarium
After playing the BMO Pavilion right before Japanese Breakfast during 2025’s Summerfest and opening for The Decemberists at Riverside Theater in 2024, Chicago’s own Ratboys will come to the decidedly more intimate Vivarium for a headlining set some six weeks removed from the release of its album, Singin’ To An Empty Chair. The indie rockers will be preceded by Florry.