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 first three official days.

Thursday, September 2

HEADLINER

T-Pain — 10 p.m. @ UScellular Connection Stage
With all due respect to Luke Bryan and REO Speedwagon, T-Pain takes the cake among headliners on Summerfest’s true opening night. Well, unless Blizzard Man is added to the lineup at the last minute. The veteran singer/rapper, emperor of auto-tune, and Big Gig regular will end Summerfest’s first day in style with a performance chock full of his hits. We promise it’ll be great and, to quote Blizzard Man himself, “word is bond.”

EARLY BIRD

Kurtis Blow — 4 p.m. @ UScellular Connection Stage
If you don’t know who hip-hop pioneer Kurtis Blow is, watch this video below, clear your calendar, and make plans to head over to the UScellular Connection Stage on Thursday afternoon. We’ll save you a spot by us.

LOCAL

You Win !!! — 6:45 p.m. @ Johnson Controls World Stage
Last fall, we formally introduced you to You Win !!!, the young project consisting of multi-talented Milwaukee musician Amanda Huff and producer William Gardiner (who releases music under the moniker of This Random Machine). The dark pop/trip-hop duo followed the news of that exciting and ambitious collaboration with a few single releases and music video premieres, but very little in the way of live and in-person performances to this point. That will change on September 2 when You Win !!! will treat those in and around the Johnson Controls World Stage to live versions of their three previously-released songs and lots of material the public has never heard before.

DEAL/TIP

All patrons who arrive between 12:00 p.m. – 3:00 p.m. and donate three (3) healthy non-perishable food items will receive one (1) FREE admission ticket, valid for the day and time of the promotion only. Canned peaches and pears are especially appreciated.

Friday, September 3

HEADLINER

DJ Diesel — 10 p.m. @ Miller Lite Oasis Stage
When “DJ Diesel” (better known as basketball legend, commentator, actor, guy who threw someone OVER A HOUSE in Grown Ups 2 and cultural icon Shaq) takes to the turntables on September 3, everyone in the vicinity of the Miller Lite Oasis will look like this.

EARLY BIRD

Yola — 4 p.m. @ BMO Harris Pavilion
We can’t emphasize this enough: do yourself a favor and see Yola at Summerfest. It’s not every day that a four-time Grammy nominee is considered an up-and-coming musician, but this British-born singer seems destined for even bigger and better things. Cut out of work early, take a seat in the shaded BMO Harris Pavilion, and get lost in the incredible vocals and uplifting message of Yola’s newly-released masterpiece, Stand For Myself. We’re going to guess you won’t be able to see her in the 4 p.m. slot ever again.

LOCAL

Abby Jeanne — 7:30 p.m. @ BMO Harris Pavilion
Speaking of astounding singers whose stocks are on the rise, Abby Jeanne is playing one of her first shows since very early 2019. Once you’ve had a chance to collect yourself after catching Yola’s set, head back to BMO Harris Pavilion to see one of Milwaukee’s best captivate a hometown crowd.

DEAL/TIP

The first 2,500 patrons who donate new or gently used children’s books with a $10 minimum value will receive one (1) FREE admission ticket, valid for the day and time of the promotion only. Picture books and early readers for children ages birth through ten are preferred. All books collected at the Mid Gate Promotions Booth will be donated to Next Door.

Saturday, September 4

HEADLINER

Rise Against — 10 p.m. @ Generac Power Stage
Windy City punk greats and Summerfest mainstays Rise Against will cap off a stacked Saturday lineup at the new Generac Power Stage. Show up early to enjoy Eve 6, Avenues, City Of The Weak, and Spanish Love Songs before Rise Against brings Summerfest’s first weekend home in grand fashion.

EARLY BIRD

Eve 6 — 2 p.m. @ Generac Power Stage
Though Eve 6 has recently drawn attention by way of its, uh, unique Twitter account, people forget this band actually whips ass. Even better than getting to see this long-running and accomplished alternative rock band live is getting to see them at 2 p.m. FOR FREE (more on that at the bottom of this article).

LOCAL

Zed Kenzo — 8 p.m. @ Miller Lite Oasis Stage
Those who show up early for Flor Rida’s headlining performance at the Miller Lite Oasis Stage are in for a treat. Milwaukee’s own Zed Kenzo will keep spirits high and jaws dropped with material that’s earned the transcendent rap talent an impressive reputation in her home city and far beyond.

DEAL/TIP

ALL patrons arriving between 12:00 p.m. – 3:00 p.m. on Saturday, September 4th, will be admitted for FREE! Select food vendors will offer discounts on food and beverage items.

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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