Spring is in the air in Milwaukee. The birds are singing. The trees are budding. And venues across the city are blooming with fresh shows. There’s the 15th anniversary of an iconic album, a charity concert with a Silver Slugger, a never-ending story, some seriously sad music and a formidable amount of joy to go around. Here are the 15 shows you just can’t miss in the Milwaukee Theater District and beyond this May.
Iron & Wine
May 2 | The Riverside Theater
I am thinking it’s a sign that you should go to Iron & Wine. For nearly a quarter of a century, this artist has been churning out classic albums, enchanting crowds and setting the standard for the American folk songbook. Now, for the first time since 2024, he’s coming back to Milwaukee’s Riverside Theater, touring his latest album “Hen’s Teeth,” alongside a catalog of well-loved classics.
George & Gracie: A Love Story
May 1 – June 14 | Milwaukee Rep
The world premiere of this production takes you inside the rise of one of comedy’s great power couples, George Burns and Gracie Allen. Follow the dynamic duo from aspiring vaudeville act to the height of stardom during the golden age of radio, television and film, in a celebration of a legacy that endured for more than 40 years.
ALICE (in wonderland)
May 1-3, 8-10 | Milwaukee Ballet at the Marcus Performing Arts Center
We’re all mad here. Mad for the Milwaukee Ballet’s spin on the classic fairytale. Tumble down the rabbit hole to rediscover the childlike magic that made you fall in love with this one, with explosions of colors, larger than life characters and stunning choreography that will lead you through the nonsensical Wonderland. Don’t be late, late, late for this very important date.
The Head and The Heart
May 4 | The Riverside Theater
In 2011, The Head and The Heart unleashed the debut album that shook the musical world. Becoming a seminal 2010s work, “The Head & The Heart” contained songs that became anthems and reintroduced a generation to the new standard of folk music. Now, 15 years later, the band is once again touring the no-skip album that propelled their careers, with songs like “Rivers and Roads,” “Couer D’Alene,” “Ghosts” and more at The Riverside Theater at the beginning of May.
Liz Cooper with VV Lightbody
May 8 | Cactus Club
Hailing from Nashville, Liz Cooper is an up-and-comer with a multidisciplinary talent that adds a layer of curiosity ahead of her Cactus Club performance. Her sound is psych rock with an edge, the kind of music that’s best described as three hundred red lipstick kisses, dotted with the ashes of spent cigarettes. Intimate, passionate and just a little indulgent, her latest release, “Hot Sass,” is exactly that.
Pat McCurdy
May 8 | Shark Hall
In case you missed it at the Milwaukee Film Fest, local musical troubadour Pat McCurdy is performing live at Shank Hall in May. Recently featured in “Bright Beautiful World: The Infectious Joy of Pat McCurdy,” for 50 years, Pat has brought joy to over 12,000 fans, with his enormous catalog of 600+ songs that range from lost love to French emperors of centuries past.
Copland & Twain: America 250
May 8-10 | Bradley Symphony Center
Our second world premiere of the month takes us to a performance by the Milwaukee Symphony Orchestra on Wisconsin Avenue for an all-American mashup no one saw coming. Pairing the stirring incidental tunes of Aaron Copland, the poignant critique of the shifting landscape in daily American life and the powerful majesty of the orchestra, Copland & Twain kicks off the 250th celebration of the birth of a nation with a bang. You’ll see costumed actors, projected visuals and a powerful story that challenges American identity with a little added humor.
The Neverending Story: Atreyu and the Great Quest
May 8-17 | First Stage at the Milwaukee Youth Arts Center
Do you still wake up with nightmares of Artax disappearing into the Swamps of Sadness? Well, it’s back. Escape into the surreal world of Fantastica during this First Stage production. Filled with thrills, fantasy and just enough nostalgia to reignite that youthful spark in adults and let kids’ imaginations run wild, this is one for the whole family.
The Joy Formidable
May 10 | Vivarium
This much delight, fills columns to new heights. All these things about MKE you never can tell. If you heard a whirring in your soul while you read this, you’re right where you’re meant to be. After a four-year hiatus from the Cream City, the British rock group is back, and this time they’re in the intimate setting of Vivarium on the East Side, bringing hits like “Austere,” “A Heavy Abacus,” “Little Blimp” and, of course, “Whirring” to life.
Kowan & Da Homies
May 15 | The Cooperage
Fearless improvisation is what this one is all about. It’s a fusion of jazz, funk and hip-hop that makes Kowan & Da Homies an act that’s hard to pass up. You never know what’s coming next, but the music moves forward with a flawlessness that just cascades over you and sounds so polished you’d swear it was rehearsed.
SEAROWS
May 18 | Turner Hall Ballroom
Make no bones about it, SEAROWS is sad. Heartbreakingly, devastatingly sad music that’s so fragile it lays the truth bare with its beautifully complex lyrics. Alec Duckart’s latest release, “Death in the Business of Whaling,” is a natural evolution of her earlier indie-folk releases, raising her horizons to more expansive music, while weighing themes of life, death, embodiment and the continuum in between. She brings this new chapter of her music career to Turner Hall in the middle of the month, where she makes her Milwaukee debut.
Christian Yelich Home Plate Charity Concert
May 21 | Landmark Credit Union Live
Stepping to the plate in May, we have a concert for a cause. The fourth annual Christian Yelich Home Plate Charity Concert makes its debut at Landmark Credit Union Live, bringing country music star Jake Owen, former frontman of The Fray, Isaac Slade, the Nicotine Dolls, local comedian Charlie Berens and a few surprises to the city’s newest concert venue to benefit a local nonprofit.
Damien Liriano
May 28 | Falcon Bowl
Tucked away in the Riverwest neighborhood is another outstanding venue putting on shows nearly every night of the week. This month, head to Falcon Bowl to check out Dominican artist Damien Liriano. Equal parts alternative hip-hop and electronic music, Liriano’s music is all about loving yourself through every phase of life. It creates a tension between the internal journey of self-discovery and the importance of maintaining an image that aligns with our surroundings.
Rilo Kiley
May 28 | The Riverside Theater
For the first time since they broke up nearly two decades ago, Rilo Kiley is coming back to Milwaukee. After a long hiatus, they’re blazing a reunion tour this spring. Touring the hits that made them a must-see band in the 00s with songs like “Silver Lining,” “Portions for Foxes,” “With Arms Outstretched” and so many more, Jenny Lewis, Blake Sennett, Jason Boesel and Pierre “Duke” de Reeder are back like they never left.
An Evening with Broasis
May 28 | X-Ray Arcade
Say maybe, are you gonna be the one who sees me? Cause after all, they play “Wonderwall.” There are cover bands, and then there’s an Oasis cover band, playing all the songs you missed on their globe-trotting tour last summer. This time, though, without the stadium prices, the seats 50 yards away or the traffic after the show. Just the jams you love, played by a cover band that does it best.
Adaptive Performances
Milwaukee’s performing arts scene is for every body! Don’t miss these adaptive performances across the city’s stages, giving everyone a chance to experience the magic of the theater.
ALICE (In Wonderland)
Find your seat in the Milwaukee Theater District, plan your stay and make it a dramatic getaway. Start here!
