September is a time of transition. This month finds summer officially giving way to fall. This month also signals the end of Milwaukee’s festival season. Well, that’s usually the case. This September, however, the city is making up for lost time by hosting a late edition of Summerfest. At the same time the Big Gig is happening, long-shuttered local venues will also be in full swing with oodles of touring talent coming to town.

And that’s not even factoring in the return of the Milwaukee Record Halftime Show series and the revival of our Avalon film screenings! There’s a ton of great things going on this month. Here are some shows, festivals, and other events that stand out this September. Check our Calendar section for more recommended events.

Wednesday, September 1 — Saturday, September 18
Summerfest @ Henry Maier Festival Park
The World’s Largest Music Festival is mixing things up in 2021, moving to September and staking out three Thursday-Friday-Saturday blocks instead of the traditional 11-day run. (Oh, and there’ll be a few “Wednesday Kick-Off Concerts” at the American Family Insurance Amphitheater, too.) As for the lineup, it’s pretty damn stacked: Megan Thee Stallion, Chance The Rapper, Jonas Brothers, Miley Cyrus, Dave Chappelle, and Guns N’ Roses are some of the big amphitheater names, while Black Pumas, Run The Jewels, Kesha, Wilco, and The Flaming Lips are just a few of the grounds stage highlights. Find the full lineup HERE.

Friday, September 3 and Saturday, September 4
Gareth Reynolds @ Milwaukee Improv
Brown Deer, Wisconsin native and ComedySportz alum Gareth Reynolds is best known as the co-host of The Dollop, a popular American history podcast that’s landed him a book deal and has brought him to perform in places like Iceland, Australia, throughout Europe, and all corners of the United States. On top of being a world-renowned podcast personality, as well as a writer (Arrested Development, You’re The Worst), actor (New Girl, The Goldbergs, Maron), and a huge fan of the Green Bay Packers, Reynolds is an avidly touring stand-up comedian. He’ll return to the greater Milwaukee area for a total of four performances at the newly-opened Milwaukee Improv September 3-4.

Saturday, September 11
An Evening With Steve Wynn @ URSA
Over the course of his extensive and impressive career, Steve Wynn has released more than 30 albums that are spread between his solo endeavor, The Dream Syndicate, and The Baseball Project. Along the way, he’s performed to audiences of all sizes all over the world, toured with the likes of U2 and R.E.M., composed scores for television and film, and spent time on a major record label. This month finds Wynn embarking on a solo tour that will bring him to a variety of intimate performance spaces, such as homes, yards, record stores, and (in the case of his September 11 Milwaukee stop) to URSA in Bay View.

Sunday, September 12
Armand Hammer @ Cactus Club
The year is months from being over, but it’s safe to assume Armand Hammer is responsible for making one 2021’s best albums. The rap duo joined forces with The Alchemist to make Haram, an otherworldly effort that takes their already cerebral creations to exciting, inspiring, and altogether enjoyable new territory. Celebrate a Packers Week 1 victory by heading to Cactus Club to see Armand Hammer headline this 18+ show.

Friday, September 17
Japanese Breakfast + Luna Li @ Turner Hall Ballroom
Michelle Zauner is having a year. On top of releasing Crying In H Mart, her incredible best-selling memoir (we know: we read/loved it immensely), Zauner released another Japanese Breakfast album in late spring. That record, Jubilee, takes the indie rock project all across the board stylistically and has earned every bit of the praise it’s getting from listeners and critics alike. Japanese Breakfast will face off against Summerfest with a September 17 show at Turner Hall. Luna Li opens.

WMSE’s Art & Music @ The Pritzlaff Building
After going virtual last year, WMSE’s annual Art & Music will return to being an in-person event that aims to raise funds for the listener-supported station through auctioning off more than 200 works from local artists. This year’s return to form will also feature live painters, multimedia artists, refreshments, and other surprises. Support our friends at WMSE on September 17 (a.k.a “917 Day”) and take home some art in the process.

Friday, September 17 and Saturday, September 18
Tom Segura @ The Riverside Theater
Actor, comedian, podcaster and former Mequon, Wisconsin high school student Tom Segura returns to the region for a two-night, three-show Riverside Theater residency as part of his perfectly-named “I’m Coming Everywhere” world tour.

Carmen Morales @ The Laughing Tap
Carmen Morales is no stranger to Milwaukee. After opening for South Milwaukee native Jackie Kashian during her 2019 stop at Underground Collaborative (R.I.P.!), the up-and-coming comic served as the host of the very first show in the history of The Laughing Tap. Morales will return to the Walker’s Point-based comedy club to headline a pair of shows, where she’s sure to delight an intimate audience with her hilarious and ever-evolving material, including her A+ impersonation of a Wisconsin accent.

Saturday, September 18
Daikaiju + The Eradicator, Roboman, Dislocation @ X-Ray Arcade
Even though Bay View Bash won’t be happening this year, X-Ray Arcade in nearby Cudahy is bringing a Bash favorite to its stage (and eventually into the street, probably) the night the neighborhood block party would have occurred. Joining the iconic act that’s famous for its fire-involved performances is The Eradicator—a conceptual punk band that would make any The Kids In The Hall fan proud—and openers Roboman and Dislocation. Don’t miss this.

Wednesday, September 22
Judas Priest + Sabaton @ Miller High Life Theater
What better way is there to end your summer than with a performance by Judas Priest?

Friday, September 24
Dogleg + Retirement Party, Gully Boys @ X-Ray Arcade
In early 2020, Dogleg released Melee. Now the Michigan-based emo greats finally get to play shows in belated support of that incredible album (which is one of our favorite records of last year). As if Dogleg playing an all-ages show in our neck of the woods isn’t already great enough, they’ll be joined by Retirement Party and Gully Boys. Wow!

Saturday, September 25
Fromm Petfest @ Henry Maier Festival Park
Following a one-year FURlough (sorry!) in 2020, Fromm Petfest returns to the Summerfest grounds for a day of fun for the whole family…including four-legged family members. The annual animal-focused event will take place from 10 a.m. to 6 p.m. and it’s free to attend.

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