September is a time of transition. This month finds summer officially giving way to fall. This month also signals the informal end of Milwaukee’s festival season. Though the seasonal shift brings about a decline of outdoor events in town, local clubs and theaters are escalating the volume and the caliber of talent they book in effort to keep the entertainment coming as the temperatures outside dip. That said, Milwaukee isn’t exactly ending this summer with a whimper or lurching into autumn. Between great touring talent, Bay View Bash, the start of our Halftime Show concert series, and much more, there’s a lot to keep you entertained this month. Here are 13 of our favorites.

Thursday, September 7
James Adomian @ The Laughing Tap
Though there’s a chance you don’t know who James Adomian is, you’ve almost certainty been exposed to his work in some way, shape or form. The prolific impressionist has amassed an incredible body of voiceover work and has likely made you laugh on a variety of podcasts with his A+ impersonations of public figures like Jesse Ventura and Bernie Sanders. On top of his success in those mediums, Adomian is also an excellent comedian. You can see him do his thing at The Laughing Tap on September 7 when he comes to the intimate club for a one-night-only engagement. 

Friday, September 8
Mondo Lucha @ Turner Hall
Since starting in 2008, Mondo Lucha has brought high-flying wrestling action, burlesque dancers, and live music to its annual Turner Hall showcase. Along the way, the variety show has managed to work with renowned pro wrestlers, sell out numerous shows, and become a must-attend Milwaukee event. The beloved local variety show returns to its familiar ballroom haunt September 8!

Sunday, September 10
Diana Ross @ Miller High Life Theatre
What’s there to say? Diana Ross is a legend!

Tuesday, September 12
Jason Isbell And The 400 Unit + Wednesday @ Riverside Theater
Alt-country powerhouse and one of modern music’s finest songwriters Jason Isbell returns to the familiar confines of Riverside Theater along with his 400 Unit backing band and opener Wednesday for a late-summer show in support of Isbell’s just-released (and wonderful!) Weathervanes.

Thursday, September 14
Third Space Presents: HOSTS @ Third Space Brewing
Last year, Third Space Brewing graciously added even more entertainment to Milwaukee’s well-stocked summer concert calendar by debuting its “Third Space Presents” music series on its gorgeous new outdoor deck stage. This year’s series has been bringing a wide range of outstanding Wisconsin acts to the brewery every Thursday night, and continues with a season-ending performance by HOSTS.

Saturday, September 16
Bay View Bash @ Kinnickinnic Avenue
Even though most of Milwaukee’s major festivals are now in the rear view mirror, one of the city’s biggest and best undertakings is still on the horizon. Yes, Bay View Bash will make its long-awaited return to Kinnickinnic Avenue on Saturday, September 16 for a day of live music, food and retail vendors, and fun.

Milwaukee Tacos And Tequila Festival @ Franklin Field
Do you like tacos, tequila, and world-renowned rappers who really popped off in the early 2000s? If you answered yes to even one of those questions, we have some good news for you. And if you enjoy all three of those things (and don’t mind driving to Franklin, Wisconsin to experience them), then you might be in for one of the best days of your life. Milwaukee Tacos And Tequila Festival is coming to Franklin Field for a day of tacos, tequila, and performances by “throwbacks.” Those “throwbacks” include the likes of Nelly, Fat Joe, Chingy, Petey Pablo, Mike Jones, Ying Yang Twins, Twista, and more.

Bully + Wombo @ X-Ray Arcade
While Bay View Bash happens about three miles to the north and Tacos And Tequila Festival rages a few miles to the southwest on September 16, frequent Milwaukee visitor Bully will be doing its thing in nearby Cudahy at X-Ray Arcade. Wombo will play in support of the Nashville rock outfit.

Tuesday, September 19
Mest + Authority Zero, Showoff @ X-Ray Arcade
No, you didn’t fall into a portal that sent you back to 2002, Mest and Showoff are BACK and they’re playing together at X-Ray Arcade. Hell yes! Put your top down, seat back, and roll over to the Cudahy Club in your Cadillac for what’s sure to be a great blast from the past. Ska-punk outfit Authority Zero will also perform.

Wednesday, September 20
Milwaukee Record presents ‘Drop Dead Gorgeous’ @ Avalon Theater
Get ready for pageant season by joining Milwaukee Record at Avalon Theater on Wednesday, September 20 for a very special summer-ending screening of the incomparable 1999 dark comedy Drop Dead Gorgeous. Tickets are going extremely fast, so get them while you still can. This will sell out.

Friday, September 22
Craig Robinson @ Milwaukee Improv
Beloved Office cast member, star of the great Killing It series on Peacock, and gifted musician/comedian Craig Robinson is coming to Brookfield for a total of four Milwaukee Improv performances September 22-23. What a way to end your summer and/or begin fall!

Wednesday, September 27
Nick Cave @ Riverside Theater
What’s there to say? Nick Cave is a legend!

Saturday, September 30
Ringo Starr And His All Starr Band @ Miller High Life Theatre
What’s there to say? Ringo Starr is a legend! His All Starr Band isn’t too shabby either.

About The Author

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Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.