February holds the distinction of being the year’s shortest month, one of Wisconsin’s coldest spans of time, and landing pretty much directly in the middle of winter. However, this particular February finds Milwaukee artists and venues bucking the trend of late-season boredom and Valentine’s-adjacent blues with a bevy of great events.
In the next 28 days, the city and its surrounding suburbs will play host to touring bands and comedians, Milwaukee’s favorite outdoor winter event, Mama Tried and Flat Out Friday programming, and the return of an usual Milwaukee Record event. This impressive list of late-winter happenings helps make the year’s shortest month a huge one in terms of entertainment options. Here are 15 standout events for February 2026.
Friday, February 6
WMSE’s Art & Music @ The Pritzlaff Building
For the ninth year, Art & Music—an art auction fundraiser for WMSE 91.7FM—will take place at The Pritzlaff Building and showcase art and music as a means of generating support for the public radio station. This event is billed as multisensory and immersive, touting “art, music, food, and entertainment” for the whole family. At the center is an auction of hundreds of album-sized, 12″ x 12″ pieces of original art from local and national artists.
Saturday, February 7
Mitten Fest @ Burnhearts
Over its 12-year run, Mitten Fest has earned the undisputed distinction of being Milwaukee’s favorite wintertime celebration. The sprawling block party will be coming back to Burnhearts for another installment. From noon to 8 p.m. on Saturday, February 7, Mitten Fest will heat up the neighborhood with live music, craft beer and cocktails, tasty treats from area food vendors, and philanthropy (as a means of collecting donations for Hunger Task Force).
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.
Saturday, February 14
The Great Milwaukee Can Koozie Swap & Bar Chip Bonanza @ Club Garibaldi
Join Milwaukee Record and Lakefront Brewery at Club Garibaldi on Saturday, February 14 for another installment of “The Great Milwaukee Can Koozie Swap & Bar Chip Bonanza.” From 1-4 p.m., we’ll have some tables set up in the back room of the bar to serve as a makeshift marketplace where people can make some koozie-related transactions.
Dale On Sale will also be there selling some of their unique koozie designs and printing designs on your koozies on-site for a small charge. But there’s more! Give us a drink chip—from ANY bar, restaurant, or brewery…even places that are no longer open or located outside Milwaukee—and we’ll let you spin our wheel for a chance to win prizes. Spins can also be purchased for $2 apiece. There’s NO COVER for this 21+ event. We dare you to think of a better way to spend Valentine’s Day.
Sunday, February 15
BLAX (album release) + Modern Tigers, Dana Coppa & Mike DNA, Youth Energy, Je’Love, and They Want Blood @ The Cooperage
There doesn’t seem to be much downtime for BLAX. The veteran Milwaukee hip-hop artist has spent the past few years alone releasing numerous albums, singles, videos, podcasts, and more. Oh, and don’t forget about touring! The tireless creator’s catalog will grow even more with his forthcoming album, Oneirology. The release will be celebrated during a BLAX-headlined show on Sunday, February 15 that features a stacked supporting cast consisting of Modern Tigers, Dana Coppa & Mike DNA, Youth Energy, Je’Love, and They Want Blood.
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.”
Friday, February 20 through Sunday, February 22
Flat Out Friday @ Fiserv Forum and Mama Tried @ The Rave / Eagles Ballroom
If you’re somehow unfamiliar, Flat Out Friday features motorcycle racers riding on top of a track that’s slathered in Dr. Pepper syrup and it’s awesome! This event is just one part of the Mama Tried festivities that are slated to happen at various local spots in mid-February. The Mama Tried Motorcycle Show itself will take place at The Rave February 21-22.
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.