12 Things to Do in Milwaukee This Weekend: May 5-7

Check out local Kentucky Derby parties, 414 Flea’s summer series, Hadestown and more.

1. Hadestown

ALL WEEKEND | UIHLIEN HALL MARCUS CENTER

It’s the last weekend to see Hadestown, a touring musical that is a retelling of the classic Greek myth of Orpheus and Eurydice set in the hellish Hadestown. The Broadway production received critical acclaim and won eight Tony awards including Best Musical and Best Original Score

2. Frankie Valli and The Four Seasons

FRIDAY AT 8 P.M. | RIVERSIDE THEATER 

With classic hits, such as “Can’t Take My Eyes Off You,” “Who Loves You” and “Walk Like a Man,” Frankie Valli and his band are making a stop in Milwaukee. Tickets are available online for this night of oldies. 


 

Nominations are open for the 2024 Unity Awards! 

Know an individual or group committed to bridging divides in our community? Nominate them for a Unity Award by Oct. 31.


3. Milwaukee Psych Fest 

FRIDAY AND SATURDAY | THE COOPERAGE 

The eighth-annual Milwaukee Psych Fest returns to The Cooperage for a three day celebration of psych music. Several local bands and acts coming from as far as Japan, France and Mexico will be playing in this mega music festival. Check out the schedule for each day to pick between an all-weekend pass or day-to-day tickets. 

4. John Caparulo

FRIDAY AND SATURDAY | THE LAUGHING TAP

Comedian John Caparulo is spending the weekend in the Brew City performing five live sets for audiences at The Laughing Tap. The midwesterner, who is known for his blue collar comedy, has performed in the Just For Laughs comedy Festival, The Tonight Show and Chelsea Handler’s old show Chelsea Lately. 

5. Kentucky Derby Parties

SATURDAY | MULTIPLE LOCATIONS

Don your biggest hat for this weekend’s several celebrations of the Kentucky Derby. Bars and venues across the city will be showing the event with plenty of drink and food specials (mint julips, anyone?). If you want to get really fancy, head down to Saint Kate – The Arts Hotel for the Woodford Reserve “Get Down and Derby” party. Bluegrass band Genesee Ridge Band will be playing and each mint julep you purchase will earn you a raffle ticket to win various prizes. And you’ll also have the opportunity to enter a contest for Best Dressed and Best Hat, to win a one-night stay at the downtown hotel. 

6. Maple Syrup: Beyond Breakfast & Into the Bar

SATURDAY AT 3 P.M. AND 5 P.M | NORTH AVENUE MARKET

The folks at Bittercube and Tapped Maple Syrup are celebrating the versatility of this great ingredient with a “Maple Syrup: Beyond Breakfast & Into the Bar” class. This 90-minute course teaches participants all about the production process and how to use maple syrup in their favorite cocktails (while sampling, of course).

7. Milwaukee Tacos and Margs Crawl

SATURDAY AT 2 P.M. | BROTHER’S BAR & GRILL

If you never miss a taco Tuesday, you’re going to want to participate in this weekend’s Tacos & Margs Crawl in celebration of Cinco de Mayo. Start at Brothers Bar & Grill and travel to Taco Mikes, Lucky Clover Irish Pub, Red Rock Saloon and other participating venues for one-of-a-kind margarita creations and taco specials. 

8. ‘Mother of All Crawls’ Waukesha Art Crawl 

SATURDAY FROM 2-8 P.M. | DOWNTOWN WAUKESHA 

The streets of downtown Waukesha will come alive on Saturday for the “Mother of All Crawls” Art Crawl. Hundreds of artists will line over 20 galleries selling homemade art and wares. While you’re browsing, grab a drink or lunch from local restaurants and shop the downtown boutiques for a true “choose your own adventure” afternoon of creativity.

9. 414 Flea Summer Series

SUNDAY FROM 11 A.M.-5 P.M. | ZÓCALO FOOD PARK

The popular 414 Flea is back for its summer series at Zócalo, bringing tons of vintage clothing and home goods, homemade jewelry and original artwork from over 40 small businesses. Make an afternoon of it and grab a drink at the food park or enjoy a meal from one of the eight different food trucks. 

10. 53212 Marketplace – Mother’s Day Edition 2023

SUNDAY FROM 11 A.M.-4 P.M. | WEST RIVER COLLECTIVE  

The 53212 Marketplace brings together creative artists and artisans in a one-stop-shop for local shoppers. Get ahead of Mother’s Day shopping with a stop at this market, which features over 25 vendors selling unique art, jewelry, candles, home goods, body products and more. Grab a brew at Amorphic Beer to further support Riverworks – one dollar of each purchase will go toward revitalization efforts in Harambee and Riverwest. 

11. Fernwood Arts Fest 

SUNDAY FROM 10 A.M. – 4 P.M. | FERNWOOD MONTESSORI SCHOOL 

Bring the kids for this family-friendly arts festival that supports public montessori schools. Students of Fernwood alongside several professional vendors will be selling their crafts just in time for Mother’s Day and Teacher’s Appreciation Week. There will also be activities for the small ones, a bake sale and live music to keep the whole fam entertained. 

12. MARNmentee Talk Back 

SUNDAY AT 3 P.M. | MARN

The Milwaukee Artist Resource Network (MARN) has been a mainstay in the city for over two decades, supporting and connecting regional artists. This Sunday, they are hosting an installment of “mentee talk back” where exhibiting artists and mentees KT Mullen, Allison Alexander Westbrook IV, Abbey Gagne, MK Widener, Colin Mitchell and Reese Rousseau with share their MARn experiences with the audience and host a Q&A about how to get involved for next season. 


Want more great Milwaukee events? Check out our calendar

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Carmella is a writer and journalist. When she's not typing behind the computer, you can catch her at a local show or thrift store.