Summerfest officially kicks off today. Over the course of nine September nights (plus a few affiliated AmFam Amphitheater shows other nights this month), hundreds of local, national, and internationally-known musicians will take to 11 stages…plus some side stages by the lake. Forced to compete with an event billed as the “World’s Largest Music Festival,” venues across Milwaukee usually tend to either significantly slow their concert schedule or absolutely vacate their stages during the colossal cluster of concerts at Henry Maier Festival Park. But this isn’t a normal year by any means.

With live, in-person entertainment finally able to safely return, venues in and around Milwaukee are hosting concerts, comedy shows, block parties, and other events during Summerfest’s run. For those who need a night or two away from the Big Gig, Milwaukee Record has scrounged up some recommendations for 40 standout shows that are happening outside the Summerfest umbrella.

Thursday, September 2

Rainbow Summer: De La Buena @ Marcus Center Grounds
After taking last summer off from live, in-person events at its gorgeous Peck Pavilion, Marcus Center has brought concerts and family-friendly film screenings back in 2021. Moreover, they’ve done so by reviving the “Rainbow Summer” series, which Marcus Center says was the city’s “original outdoor entertainment series.” One of Rainbow Summer’s last installments of the year is also one of its best, as De La Buena brings its world-class world music to the pavilion for a free performance.

Mr. Nice Guy Presents: Kyle Kenowski + Weird Storm, Fressure Point, Anson Obvious @ Cactus Club
Tireless writer, podcaster, and champion of Milwaukee music Ben “Mr. Nice Guy” Slowey has put together quite the local lineup for this Cactus Club show that coincides with Summerfest’s true opening night. Unless you’re dead set on seeing T-Pain or REO Speedwagon tonight, you should strongly consider checking this out.

Alternative Radio + Diet Lite, The Nile Club, Groundlings @ X-Ray Arcade

Friday, September 3

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.

Gold Steps + Walt Hamburger, Fun Bois @ X-Ray Arcade
Even though original headliner, The Dollyrots, canceled their tour on account of COVID concerns, the September 3 show will still go on at X-Ray Arcade. Gold Steps was promoted to the head honcho role, with Appleton troubadour Walt Hamburger moving to the middle of the pack, and Fun Bois being added as the opener. Even without The Dollyrots, this is a solid lineup!

Kainalu + Immortal Girlfriend @ The Back Room @ Colectivo

John Egan @ The Laughing Tap

Saturday, September 4

The Sugar Maple Comedy Show: Kenny DeForest @ The Sugar Maple
After a long time off, The Sugar Maple Comedy Show is back! The monthly showcase will return in style with accomplished comedian, writer, and actor Kenny DeForest. Buy a ticket, laugh it up, and enjoy a few pints at one of Milwaukee’s best beer bars.

B.J. Seidel + Joe Crockett @ The Tonic Tavern
On Saturday afternoon, The Tonic Tavern in Bay View will host a pair of Milwaukee’s best singer-songwriters as part of its “Gigs 4 Good” charity concert series. Listen to B.J. Seidel and Crockett play solo material and stripped-down renditions of songs they wrote for Decibully, Dramatic Lovers, The Championship, and Rx Drugs.

Brief Candles + Haunter, Gauss @ Club Timbuktu

Vivica Fox + Kelly Kellz: Funny By Nature Comedy Tour @ Turner Hall

John Egan @ The Laughing Tap

Gareth Reynolds @ Milwaukee Improv

Tinder Live! With Lane Moore @ The Back Room @ Colectivo

Thursday, September 9

Rainbow Summer: DLC Dance @ Marcus Center Grounds
After a few months of concerts, film screenings, and other types of family-friendly entertainment, Marcus Center’s “Rainbow Summer” series is nearing its end. The penultimate performance finds DLC Dance taking to the Peck Pavilion for a free Thursday night show.

In The Pines + Rookie @ Cactus Club

Friday, September 10

Sad Summer Festival @ The Rave/Eagles Ballroom
Something this sad never sounded so good. The Rave/Eagles Ballroom will play host to a so-called “Sad Summer Festival” that features performances by All Time Low, The Story So Far, Movements, The Maine, Grayscale, and Destory Boys.

D.L. Hughley @ Milwaukee Improv
The Hughley Show namesake, one of the “Original Kings Of Comedy” and veteran stand-up D.L. Hughley will break in the Milwaukee Improv when he performs five shows in the new Brookfield-based club September 10-12.

Matty Ryan @ The Laughing Tap

Bianca Del Rio @ Pabst Theater

Alan Jackson @ Fiserv Forum

Jo Koy @ Riverside Theater

Kathleen Edwards @ The Back Room @ Colectivo

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.

Silver City International Festival @ Arlington Heights Park
Since its start in 2012, Silver City International Festival has celebrated the numerous cultures that help make Silver City the most diverse neighborhood in Milwaukee through food, the arts, and music. After taking the year off from hosting the event in its traditional sense, we’re please to report Silver City International Festival will make its triumphant return. This year’s festival will take place from noon-5 p.m. at Arlington Heights Park (3429 W. Pierce St.) on Saturday, September 11.

Iliza @ The Riverside Theater

D.L. Hughley @ Milwaukee Improv

Matty Ryan @ The Laughing Tap

Thursday, September 16

Rainbow Summer: Terrance Simien & the Zydeco Experience @ Marcus Center Grounds
Rainbow Summer ends with a bang, as Terrance Simien & the Zydeco Experience treats Peck Pavilion attendees to a free performance on Thursday, September 16.

49 Winchester @ The Back Room @ Colectivo

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/absolutely loved it), 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.

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.

Jay Mohr @ Milwaukee Improv

Carmen Morales @ The Laughing Tap

Tuba Skinny @ The Back Room @ Colectivo

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.

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.

Tom Segura @ The Riverside Theater

Jay Mohr @ Milwaukee Improv

About The Author

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.

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