Remember when the end of summer was also kinda-sorta a signal for things slowing down in Milwaukee entertainment? Those were simpler (and much more boring) times. Thankfully, there are also a ton of musicians, comedians, and other entertainers coming to town during the first full month of fall. And that’s not even counting recurring Milwaukee Record events like our Halftime Show series, Avalon film screenings, and Midweek Music concerts. Here are 17 standouts from the bunch.
Friday, October 2
Kyle Gordon @ Falcon Hall
On Friday, October 2 (the very same day his new album, Kyle Gordon Is Everywhere, comes out), Kyle Gordon will take the stage at Falcon Hall to treat fans of music, comedy, and musical comedy to what’s sure to be an unforgettable performance. Will Barry Bergen make an appearance? Only time will tell. But yeah, he probably will.
Saturday, October 3
Beet Street Harvest Festival @ Cactus Club
The Bay View block party—hosted by Cactus Club, Palomino, and Goodkind—is set to bring about a day of live music, local food and retail vendors, community organizations, and pie-based competition to a parcel of Wentworth and Potter avenues outside the aforementioned businesses. The family-friendly event will run from 1-7 p.m., with an 18+ after party to take place at Cactus Club once Beet Street concludes. See the whole music, food and vendor lineup HERE.
Monday, October 5
The Roast Of Milwaukee @ The Cooperage
Milwaukee Record’s long-running Roast Of Milwaukee event is back! Like previous years, the event—which is done in association with the Milwaukee Comedy Festival—will feature a stacked cast of local comedians gently (or, in some cases, viciously) making fun of our fair city. Joining the homegrown humorists is host sports radio personality/comedian Ramie Makhlouf, as well as a handful of surprises. And the laughs won’t just be at the expense of Milwaukee. A portion of the show’s proceeds will be donated to Milwaukee Women’s Center.
Monday, October 5 through Sunday, October 11
Milwaukee Comedy Festival @ various locations
Originating long before the city had anything resembling a sustainable comedy community, Milwaukee Comedy Festival has grown and evolved along with Milwaukee’s stand up scene. Along the way, festival has also brought in a wealth of noted national talent to headline some of its shows. This year’s edition—which will be taking place over a span of 11 shows at five different venues October 5-11—is no different, as accomplished comedians such as Shane Torres, Mike Lebovitz, and Vik Pandya are among the performers taking the stage during the 21st annual Milwaukee Comedy Festival.
Tuesday, October 6
Beck @ Landmark Credit Union Live
ALERT! ALERT! New-ish Milwaukee venue Landmark Credit Union Live is hosting a show that folks who say they’ll never go to Landmark Credit Union Live due to its ties to Live Nation and Ticketmaster may actually want to go to! It’s Beck. Yes, Beck is scheduled to bring his Ride Lonesome Tour to Landmark Credit Union Live Tuesday, October 6. It will be Beck’s first Milwaukee show in nine years. (Ha, we totally forgot we were at the last Riverside Theater show.)
Wednesday, October 7
Weezer + The Shins, Silversun Pickups @ Fiserv Forum
Weezer will be coming to Fiserv Forum on Wednesday, October 7! It will be the legendary alternative rock band’s first show in Milwaukee in more than five years, and their first show at the arena ever. This concert is part of an utterly stacked tour called “The Gathering” that also features opening support from The Shins and Silversun Pickups. We’ll see you there!
Wednesday, October 7
Rhett Miller + Louie Luchchesi & Mike Benign @ Shank Hall
Americana legend Rhett Miller has been a member of Old 97’s for close to 35 years and, along the way, he’s released nine solo albums. Miller’s latest album, A Lifetime Of Riding At Night, came out last year (and few months before the 97’s played Summerfest this year). On October 7, the well-traveled troubadour will come back to Milwaukee to play songs off that record, cuts from his numerous other solo releases, Old 97’s material, and more at Shank Hall.
Thursday, October 8
Robby Hoffman @ Turner Hall
If you somehow aren’t aware of Robby Hoffman yet, get ready to be hearing and seeing a lot of her. On top of being an award-winning comedy writer and a busy TV actor (who you might’ve seen on Hacks, Rooster, and Dying For Sex), Hoffman is an outstanding stand up comedian on the verge of breaking out. Less than a year removed for the release of her John Mulaney-directed Netflix special entitled WAKE UP, Hoffman will swing by Turner Hall. Go for the laughs, as well as the probable “I saw her at Turner Hall” bragging rights when she’s playing a far bigger room the next time she’s in town.
Saturday, October 10
Anthony Jeselnik @ Riverside Theater
Respected roaster, master of dark humor, and The Jeselnik Offensive namesake Anthony Jeselnik has released a total of five comedy specials over the course of his nearly quarter-century comedy career. The most recent among them, Bones And All, was filmed at Pabst Theater in April 2024 and released on Netflix later that same year. He’ll return to Milwaukee as part of his “Wrath Of Man” tour.
Saturday, October 10
Rise Against + Alkaline Trio, Teen Mortgage @ The Rave/Eagles Club
Hell yeah! On Saturday, October 10, Rise Against and Alkaline Trio—a pair of veteran Chicago-born alternative rock acts with punk sensibilities—will join forces to each play their decades worth of beloved material at The Rave. As if you need another reason to go, great D.C. punk duo Teen Mortgage will open.
Saturday, October 10
Flannel Fest @ Boone & Crockett / The Cooperage
Boone & Crockett’s “Flannel Fest” will return on Saturday, October 10. Enjoy live music, food vendors, and local retailers in the Boone/Cooperage lot during this free, family-friendly festival. HERE is the full entertainment lineup.
Sunday, October 11
Harrison Gordon + Liquid Mike, and Excuse Me, Who Are You? @ X-Ray Arcade
Illinois emo-tinged punk project Harrison Gordon—who just release a new album with a song called “Milwaukee Josh” on it—will once again take the stage at the familiar confines of X-Ray Arcade. They’ll be joined by excellent U.P. indie outfit Liquid Mike and Madison’s own Excuse Me, Who Are You? For a can’t-miss Sunday night soiree in the heart of Cudahy.
Monday, October 12
Armand Hammer + Quelle Chris @ X-Ray Arcade
When New York-based rappers Elucid and Billy Woods join forces, they become Armand Hammer. A few years removed from performing at Cactus Club, the acclaimed, influential, experimental, and incomparable hip-hip duo will return to the region to head up a Monday, October 12 show at X-Ray Arcade, Quelle Chris opens.
Friday, October 16
Ben Schwartz & Friends @ Riverside Theater
Ben Schwartz—an accomplished actor, improvisor, and the voice of a certain speedy blue hedgehog—will come to Milwaukee with some of his improv-inclined pals for what’s sure to be a side-splitting night of improv during the “Ben Schwartz & Friends” show.
Saturday, October 17
“Weird Al” Yankovic + Puddles Pity Party @ Fiserv Forum
It’s been more than three years since Alfred Matthew “Weird Al” Yankovic graced a Milwaukee stage and delighted fans with his beloved parody (and original!) songs about food, the internet, Star Wars, and the benefits of sticking your head in the microwave and getting yourself a tan. But all that will change on Saturday, October 17 when Weird Al brings his “Bigger & Weirder” tour to Milwaukee’s Fiserv Forum. And yes, we’re bringing back our beloved Weird Al Week to coincide with the Weird Al show! YES YES IT’S ALL TRUE WE JUST DON’T KNOW WHAT’S WRONG WITH US!
Saturday, October 17
Inside A Dream: The Music Of David Lynch @ The Argo
Following a few prior impressive re-imaginings of music from films by the late, great David Lynch, the “Inside A Dream” showcase will take the stage at The Argo. Expect renditions of compositions Lynch fans will surely recognize from works like Twin Peaks, Blue Velvet, Mulholland Drive, and more.
Wednesday, October 21
Sylvan Esso @ Riverside Theater
What can we say about Sylvan Esso at this point? The electropop duo met in Milwaukee (where member Nick Sanborn lived for many years). They’re awesome. They’re a few weeks removed from an absolutely enjoyable headlining DJ set a WMSE’s Backyard BBQ. They just put out an outstanding new album. They’re performing at Riverside Theater on Wednesday, October 21 in support of that outstanding new album. Does that about cover it?