Summerfest! The World’s Largest Music Festival mixed things up in 2021, moved to September and has staked out three Thursday-Friday-Saturday blocks instead of the traditional 11-day run. (Oh, and there were a few “Wednesday Kick-Off Concerts” at the American Family Insurance Amphitheater, too.) With that much entertainment packed into such a tight window, we understand if you’re stressing about how to Fest to the best of your ability.

In an effort to help you make some potentially difficult Summerfest decisions, Milwaukee Record will offer some Record Recommendations for all three weekends of Summerfest, including a suggested headliner, a reason to show up early, a can’t-miss local act, and a tip for a way to have a cheaper and/or better experience. With two weekends already in the books, here are our Record Recommendations for Summerfest’s final week.

Thursday, September 16

HEADLINER

Megan Thee Stallion — 7:30 p.m. @ American Family Insurance Ampitheater
It’s Megan Thee Stallion’s world and we’re all just living in it. Since the beginning of 2020, the talented Texas rapper has collaborated with the likes of Beyoncé and Cardi B, put out some of the most popular songs on the planet, earned three Grammy Awards (including Best New Artist) and a spot on TIME‘s list of the 100 most influential people in the world, and has become a household name. After that whirlwind year-plus, Megan is finally able to perform her award-winning material live in front of the millions of fans she’s gained over the last 18 months. You can see her at American Family Insurance Ampitheater Thursday night. Polo G opens.

EARLY BIRD

Spin Doctors — 4:30 p.m. @ Uline Warehouse Stage
Say, if you grew up in the ’90s, just go ahead now. If you can leave work by 3:30, just go ahead now. If you got some extra dollars (or are 60 or older, making you eligible for free entry), just go ahead now. If you want to see Spin Doctors, just go ahead now.

LOCAL

GGOOLLDD — 4 p.m. @ Briggs & Stratton Big Backyard
Way back in February of 2020, the Milwaukee/Louisiana dance-pop purveyors in GGOOLLDD released Here We Are, an excellent album that earned mention on our end-of-year best music list. Sadly, that record has yet to get a true release show, as the band rescheduled its Turner Hall date a few times before ultimately canceling it altogether. Now, more than 18 months later, GGOOLLDD will finally be able to perform songs from Here We Are (as well as tracks from its entire catalog) when they take the stage at Briggs & Stratton Big Backyard at 4 p.m. this Thursday. Honestly, September 16 is the most stacked day/night for local music for this year’s Summerfest, but we think this show takes the cake.

DEAL/TIP

All patrons ages 60+ will be admitted for FREE when they present their ID at the designated turnstile at any gate. Admitted seniors will also receive a voucher for $2 off of a food or non-alcoholic beverage purchase over $10. Spend the day enjoying music spanning a range of genres from The Grass Roots, Tower of Power, the Direct Supply Golden Idols, and more. Interact with over 25 senior-focused resource booths near the South Gate.

Friday, September 17

HEADLINER

Run The Jewels — 10:15 p.m. @ Generac Power Stage
Every single Summerfest, there’s one “Festival Stage” booking that seems far too big for a grounds stage and way better-suited for the Amphitheater. But since Miley Cyrus and Wiz Khalifa are already playing the AmFam this Friday night, it looks like everyone who walks through the Summerfest gates will be able to see Run The Jewels. While we’re sure this recommendation will only add to the Imagine Dragons-like turnout at the Generac Power Stage, we still think Killer Mike and El-P will deliver Summerfest’s set of the night. Show up early to claim a good spot, be good to one another, and have fun.

EARLY BIRD

Nora Collins — 6 p.m. @ UScellular Connection Stage
Even though Nora Collins currently calls Nashville home, the Milwaukee-born crossover country talent could technically qualify for local distinction. Regardless of her local or national classification, Collins must be seen. Swing by the UScellular Connection Stage at 6 o’clock to watch her play a homecoming set, which is sure to feature cuts from Strings—her excellent 2018 EP—and her brand new single called “Vegas.”

LOCAL

WebsterX — 6:30 p.m. @ Generac Power Stage
Speaking of local musicians with the potential of national appeal, accomplished Milwaukee rapper WebsterX will do his city proud (yet again) when he takes the Generac Power Stage a few hours before Run The Jewels performs. Whether you’re going specifically to see him or you’re just showing up early to hold your spot for that night’s headliner, you’re going to enjoy WebsterX.

DEAL/TIP

Pick ‘n Save and Metro Market shoppers who bring a receipt dated September 15-17, 2021, to any gate during the last weekend of Summerfest (Thursday – Saturday) between the hours of noon and 7 p.m., will receive two general admission tickets, valid for admission during the last weekend of Summerfest, September 16-18, 2021. Limit of two (2) receipts/per person, per day. Offer includes original register or digital receipt. Purchase must include at least one food item.

Saturday, September 18

HEADLINER

Black Pumas — 9:30 p.m. @ BMO Harris Pavilion
Austin-based soul outfit Black Pumas will treat the BMO Harris Pavilion to a performance full of the band’s multi-Grammy-nominated material. It’s been a strange-yet-great September Summefest so far, and this would be one hell of a way to bring your 2021 Big Gig experience to a close.

EARLY BIRD

Negative/Positive — 12:50 p.m. @ UScellular Connection Stage
Oh, how the years fly by! Negative/Positive—a Girls Rock Milwaukee success story that started when the band’s members were literally children—is now wrapping up what’s being called “The Graduation Tour” with a pre-college-enrollment stop at Summerfest. Though it’s not officially the end of Negative/Positive, the band says the early afternoon show will be its “last gig for a good while.” You’ve been warned!

LOCAL

Something To Do — 2 p.m. @ UScellular Connection Stage
Yeah, yeah…we know Negative/Positive is a local band as well, but once they’re done playing on Saturday, we highly recommend staying put and watching veteran Milwaukee-Madison ska-punk outfit Something To Do. They’re so good and super fun. You’ll be glad you stayed.

DEAL/TIP

All patrons arriving between 12:00 p.m. – 3:00 p.m. will be admitted FREE, compliments of Summerfest!

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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