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, a special screening of a 2004 classic, Mama Tried and Flat Out Friday programming, and more. This impressive list of late-winter happenings all help make the year’s shortest month a huge one in terms of entertainment options. Here are 15 standout events for February 2025.

Saturday, February 1 (also Friday, January 31)
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 last February, Mitten Fest will return to its rightful home outside of Burnhearts in Bay View. Bundle up for a full day of live music, rare beer releases, local food and retail vendors, charity, and wintertime fun.

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
WMSE’s Art & Music @ Pritzlaff Building
For the eighth 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 multi-sensory and immersive, touting “art, music, and good vibes” for the whole family. The art will come in the form of 175 pieces that were made local artists and are up for auction. Music will come from WMSE DJs and Nineteen Thirteen. There will also be food available from area food trucks, as well as refreshments from local breweries and distilleries on sale.

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 two shows on February 8.

Collections Of Colonies Of Bees + Alicia Rytlewski, Field Report @ Pabst Theater
Pabst Theater Group’s “$10 Buck Show” returns in grand fashion, as an outstanding grouping of Milwaukee acts will play at The Pabst Theater. Collection Of Colonies Of Bees will head things up, with opening support from Alicia Rytlewski (playing the release show for her debut album), and Field Report. That’s one heck of a show, especially for only $10!

Friday, February 14
3rd Annual Lonely Hearts HonkeyTonk @ Cactus Club
The third annual Lonely Hearts Honky Tonk brings some of the city’s best musicians in the folk/Americana/country realms together at Cactus Club for one can’t-miss Valentine’s Day showcase. This year’s event includes “sad country songs” from the likes of Kati Katchever, J.R. Wesley, The Krause Family Trio, Ellie Jackson, The Spine Stealers, and Maximiano.

Friday, February 14 and Saturday, February 15
All Messed Up XIII @ Linneman’s Riverwest Inn
All hail the return of Milwaukee’s “annual randomized musical experiment,” All Messed Up! The two-night extravaganza will feature a total of 16 new bands that were created via random drawing back in December. Friday night showcases the musical stylings of Pjörk, RSTLNE!, The New Jersey Drones, and Soups Totes DuJour.

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.

Saturday, February 15
Chris Novak Birthday Extravaganza @ The Cooperage
Milwaukee music super-fan and all-around great guy Christopher Novak has long celebrated his birthday by giving local listeners a gift in the form of one heck of a concert. This year’s loaded lineup includes Gold Steps, Colfax Speed Queen, Alley Eyes, and Mari Mari taking the stage at The Cooperage.

Wednesday, February 19
Milwaukee Record presents ’50 First Dates’ @ Avalon Theater
50 First Dates tells a tale as old as time: swinging bachelor marine veterinarian (Adam Sandler) falls for beautiful art teacher with anterograde amnesia (Drew Barrymore). Romantic hijinks—a.k.a. Sandler repeatedly having to woo Barrymore because she can’t remember him from day to day—ensue. Think of it like Groundhog Day, but set in Hawaii and starring the ’90s/’00s cinematic power couple from The Wedding Singer. Also, Sean Astin, Dan Aykroyd, and Rob Schneider are in it.

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.

Friday, February 21 through Sunday, February 23
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 21-23.

Sunday, February 23
Wückfinter VII @ Ray’s Wine & Spirits
On Sunday, February 23, Ray’s will host the seventh annual Wückfinter. From 12-5 p.m., the lot outside the store will feature a wide range of 3 Floyds beers (including some rarities) on tap. Bavette, La Dama, Morel, and Offshore will be on-site to serve up food, and DJ Fuzzy Logic will handle the music. Save the date for what’s sure to be a wücking good time in the Rayborhood.

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!”