Summerfest! 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.) 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. Here are our Record Recommendations for Summerfest’s second week.

Thursday, September 9

HEADLINER

Chris Stapleton + Sheryl Crow — 7:30 p.m. @ American Family Insurance Ampitheater
Crossover country star, five-time Grammy winner, and prolific songwriter Chris Stapleton is well worth the price of admission on his own, but having Sheryl Crow as the opener helps make this a must-attend AmFam Ampitheater affair. The Bucks fan, long-tenured musical legend, and at least one-time Milwaukee Record reader will kick things off at 7:30 p.m. before Stapleton brings the show home. Hopefully Bobby Portis shows up, too.

EARLY BIRD

Everclear — 4 p.m. @ Miller Lite Oasis Stage
From the very same publication that brought you a glowing review of Eve 6’s recent 2 p.m. Summerfest set now comes…a recommendation to get to Henry Maier Festival Park on Thursday to catch an early set by Everclear. And if you need a drink pairing for the catchy radio rock hits of yesteryear you’ll be hearing at the Miller Lite Oasis Stage, it’s worth mentioning all beverages will be half off from 12-6 p.m. To quote Everclear singer Art Alexakis, “Yeah! Yeah! Ooo, yeah!”

LOCAL

Peter Mulvey + SistaStrings — 6:45 p.m. @ Johnson Controls World Stage
Last year, Peter Mulvey and SistaStrings joined forces to release Live At Cafe Carpe, a remarkable live album. This year, they’ll come together again to share the stage at Summerfest. Don’t miss this one. It’s going to be something special.

DEAL/TIP

Enjoy a collection of music through the decades from artists including Everclear, DJ Jazzy Jeff, Third World, and more. From 12:00 p.m. – 6:00 p.m., all beverages will be 50% off (excluding frozen drinks, specialty coffee drinks, and smoothies).

Friday, September 10

HEADLINER

Wilco — 9:45 p.m. @ Miller Lite Oasis Stage
What’s there to say here? It’s Wilco! It’s Summerfest! It’s going to be great. Be there.

EARLY BIRD

Revenge Of The 80s + Daughters Of Comedy — 6:30 p.m. @ Uline Warehouse Stage
Believe it or not, standup comedy used to have a noticeable presence at Summerfest. Well, the art form is finally making its way back to the Big Gig this weekend after a looooong absence. On Saturday, Dave Chappelle will treat American Family Insurance Ampitheater to a headlining performance (more on that later in this article). A day earlier, Uline Warehouse Stage will bring the laughs with a “Daughters Of Comedy” showcase that features Mindy Rickles (daughter of Don Rickles) and Camilla Cleese (John Cleese’s daughter) and a “Revenge Of The 80s” performance with Mark “Skippy” Price and Michael Winslow. The latter is a human sound effects machine you and/or your parents might recognize from his role in the Police Academy movies.

LOCAL

Trapper Schoepp — 8 p.m. @ Miller Lite Oasis Stage
Remember earlier when we encouraged you to see Wilco? That hasn’t changed, and while you’re at it, you should probably make sure to show up early to catch Milwaukee troubadour Trapper Schoepp playing an 8 p.m. opening set in support of Wilco.

DEAL/TIP

The first 1,500 patrons who arrive between 12:00 p.m. – 3:00 p.m. and donate hygiene supplies like deodorant, shampoo, and body wash with a total minimum value of $10 will receive one (1) FREE admission ticket, valid for the day and time of the promotion only. All donations benefit United Way of Greater Milwaukee and Waukesha County’s community schools.

Saturday, September 11

HEADLINER

Kesha — 10:15 @ BMO Harris Pavilion
A few years removed from her last Summerfest stop, Kesha is coming back! Don’t miss the certified pop star, award-winning songwriter, activist, and fan of The Rave when she closes out the festival’s sixth night with what’s sure to be a memorable and all-around amazing performance. Let’s make the most of the night like…we’re living between waves of a pandemic.

EARLY BIRD

Dave Chappelle — 7:30 p.m. @ American Family Insurance Ampitheater
Does 7:30 p.m. qualify as “early” or are we grasping at straws here? Either way, don’t miss Dave Chappelle in this full-on ampitheater performance. And if this one is either too late or too pricey for you, then we urge you to see Living Colour at Uline Warehouse Stage at 6:30 p.m.

LOCAL

Klassik — 6:45 p.m. @ Johnson Controls World Stage
Klassik is a tireless Milwaukee rapper, producer, vocalist, multi-instrumentalist, and downright musical force who has earned a sterling artistic reputation in his home state (and far beyond). Don’t miss your chance to see a local favorite win over a packed Johnson Controls World Stage this Saturday evening and to see what he’s been working on the past 18 months. You’re in for a treat.

DEAL/TIP

All active-duty military personnel and veterans, along with up to four (4) family members, who present their Military ID at the designated turnstile at any gate will be admitted for FREE.

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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