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. Beyond massive outdoor undertakings like Mitten Fest and Wückfinter, Milwaukee and its surrounding suburbs will play host to touring bands and comedians, a special screening of a ’90s 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 2023.

Thursday, February 2 through Sunday, February 5
Wes Fest: A Wes Anderson Themed Pop Up & Art Show @ The Sugar Maple
Less than four months removed from its Studio Ghibli “immersive experience,” The Sugar Maple will undergo another ambitious transformation. From February 2-5, the Bay View bar will host Wes Fest. The “Wes Anderson Themed Pop Up & Art Show” will feature local art honoring the work of the iconic director. In addition to the artistic aspect, The Sugar Maple will change up its decor and update its cocktail list for the four-day affair. There will also be a costume contest, a vendor fair, Wes-related food options, and much more.

Friday, February 3 through Sunday, February 5
Anime Milwaukee @ Hilton Milwaukee City Center Hotel
What started as a college anime club meeting has blossomed into a massive three-day convention that annually brings hundreds of folks to the Hilton in Downtown Milwaukee to celebrate “anime, manga, Asian culture, music and gaming.” Anime Milwaukee will make its in-person return February 3-5.

Friday, February 3 and Saturday, February 4
Dulcé Sloan at The Laughing Tap
When you have a chance to see rising stand-up star and The Daily Show correspondent Dulcé Sloan in an intimate Walker’s Point comedy club, you take it. On Friday, February 3 and Saturday, February 4, you’ll actually have FOUR opportunities to see Sloan at The Laughing Tap.

Saturday, February 4
Mitten Fest @ Burnhearts
For a period of nine years, Burnhearts’ Mitten Fest has offered a one-day escape from the seasonal doldrums that plague Wisconsinites in wintertime. The February festival brings people together in a two-block stretch on Bay View’s Potter Avenue (and part of Logan in recent years) with a wintry mix of live music, food, beverages, and charity. After taking 2021 off for obvious reasons, Milwaukee’s favorite winter celebration made its triumphant return in early 2022. The 10th annual Mitten Fest will take place on Saturday, February 4. The music lineup and vendors for this year’s Mitten Fest can be found HERE.

Sunday, February 5
Buffalo Nichols + Stephen Hull @ Cactus Club
Since mid-2021, Buffalo Nichols—the solo project of Milwaukee native and current Austin, Texas resident Carl Nichols—has been busy. During that span, Nichols released his debut album on Fat Possum Records, toured avidly, played a number of massive music festivals, shared the stage with some massive acts, and even appeared on the Late Show With Stephen Colbert. Through it all, he’s made sure to return to Milwaukee to perform on a semi-regular basis. Speaking of that, Buffalo Nichols will be playing two shows at Cactus Club on Sunday, February 5. Local blues purveyor Stephen Hull will play in support.

Sunday, February 5
MKE Chili Bowl @ Potawatomi Hotel & Casino
After a few years away, the mighty MKE Chili Bowl is back to tickle tongues, clear sinuses, and bring a wide variety of Milwaukee-area culinary professionals together to compete for The Golden Ladle. Head to Potawatomi Hotel & Casino on Sunday, February 5 to sample traditional, spicy, and vegetarian chili varieties.

Thursday, February 9 and Friday, February 10
The Florentine Presents: Covers with Immortal Girlfriend @ The Cooperage
The Florentine Opera will join forces with sibling synthwave duo Immortal Girlfriend for two nights of re-imagined classics as part of Florentine’s “Covers” series. In addition to the genre-melding collaboration taking place on stage, The Cooperage will also have specialty “cocktails and bites” available for purchase.

Saturday, February 11
Chris Novak Extravaganza @ The Cooperage
Milwaukee music super fan and all-around great guy Christopher Novak will celebrate his birthday by giving local listeners a gift in the form of one heck of a concert. This year’s loaded lineup includes Daisychain, Wristwatch, Credentials, and Stephanie Joanna taking the stage at The Cooperage.

Thursday, February 16
Scott Seiss @ Milwaukee Improv
If you’ve spent any time on the internet over the past six-plus months, there’s a good chance you’ve seen some of Scott Seiss’ “Angry Retail Guy” videos. Beyond starring in the viral sketches, Seiss is also a stand-up comedian and actor (who you’ll see in the upcoming film Cocaine Bear). You can see him do his thing at Milwaukee Improv in nearby Brookfield on Thursday, February 16.

Friday, February 17 to Sunday, February 19
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 18-19.

Wednesday, February 22
Milwaukee Record presents ‘The Little Rascals’ @ Avalon Theater
The Little Rascals finds Spanky and the rest of the “He-Man Woman Hater’s Club” suddenly at odds with their pal Alfalfa when the latter takes an interest in Darla. Over the course of the film’s 82-minute runtime, viewers encounter a clubhouse fire, a soap box derby race, and a wealth of gags and goofs from a talented cast of child actors that folks of all ages will enjoy. The kid-friendly flick also features cameos from the likes of Mel Brooks, Lea Thompson, Daryl Hannah, Reba McEntire, Whoopi Goldberg, and (ugh) someone else you’re going to recognize.

Thursday, February 23
Rust Ring (record release) + Rat Bath, Brave You, Okay Omen @ X-Ray Arcade
In addition to her work as a member of Direct Hit! and Devon Kay & The Solutions, Joram Zbichorski also fronts a so-called “Drop C Emo Band” called Rust Ring. On Thursday, February 23, Zbichorski and her Rust Ring cohorts will celebrate the release of their new album, North To The Future, at X-Ray Arcade. Rath Bath, Brave You, and Okay Omen will join Rust Ring to further cement this show as a can’t-miss event.

Greensky Bluegrass @ Riverside Theater
Almost exactly a year removed from their last headlining appearance at Riverside Theater, veteran Kalamazoo-based Americana outfit Greensky Bluegrass will return to the historic venue (where they also helped ring in 2020 with a New Year’s Eve show) to play songs from the band’s just-released Courage For The Road: Fall 2021 live record and probably lots of cuts from their other eight studio albums as well.

Sunday, February 26
Wückfinter @ Ray’s Wine & Spirits
Prepare to wage war on the winter doldrums outside of Ray’s Wine & Spirits in late February. From noon to 5 p.m. on Sunday, February 26, the event—which is an exclusively outdoor affair—will allow patrons the chance to indulge in tons of 3 Floyds beer (including some rarities TBA) and a one-day-only 3 Floyds boozie slushie. Beyond the beer offerings, Ray’s parking lot and parts of 89th Street and 90th Street will host an impressive cast of food vendors and a DJ-curated playlist. It’s going to be a Wücking awesome day in the Rayborhood.

Tuesday, February 28
Bayside + I Am The Avalanche, Koyo @ The Rave / Eagles Club
New York punk vets Bayside will make its way back to the band’s familiar stomping grounds of The Rave. Joining them in this late-winter stop on their “Just Like Home Tour” are I Am The Avalanche and Koyo.