11 Things To Do in Milwaukee This Weekend: June 3-5

Pridefest, a comedy show, a pop-up market and more make this week’s list.

1. Art 64: Live Painting Tournament

FRIDAY AND SATURDAY | VILLAGE OF TOSA

Art lovers can watch brand new creations come to life in real time at the ART 64, a bracket-style live painting tournament. Attendees will be able to stroll through the Village of Tosa to find 64 artists painting their newest masterpieces and vote for their favorites. The competition runs from 5:30 p.m. to 10:00 p.m. on Friday and from 3:30 p.m. to 8:00 p.m. on Saturday. The tournament also features live music and food from local restaurants.

2. Theatrical Premiere of Small Town Wisconsin

FRIDAY AT 7:30 P.M. | ORIENTAL THEATRE

The award-winning dramedy about a father-son road trip from rural Wisconsin to Milwaukee is making its way onto the big screen in its favorite city. Attendees can meet the cast and crew of the film. Grab a bag of popcorn and get ready for some quality Midwestern humor.

3. Author Event for The Milwaukeean: A Tale of Tragedy and Triumph

FRIDAY AT 6:30 P.M. | BOSWELL BOOK COMPANY

The traumas and joys of growing up in Milwaukee are explored in The Milwaukeean. Joey Grihalva and Kellen ‘Klassik’ Abston will visit the bookstore to discuss and sign their new book and answer questions. While the event is free, attendees must register ahead of time to save their spot. 

4. Walker’s Point Pop-Up Market

SATURDAY FROM 10:00 A.M.-5:00 P.M.| CLOCKTOWER ANTIQUES

What goes with food trucks and music? A vintage pop-up market. Shoppers can browse products from over 30 vendors and makers at the first-ever Walker’s Point Pop-Up Market. 

5. Hops & Hounds

SATURDAY FROM 11 A.M. TO 6 P.M. | NORTH AVE. & FARWELL AVE. CORRIDOR

Upgrade your weekend walk with your dog by heading over to Hops & Hounds. This free East Side outing will have over two dozen artists and vendors, live music, henna tattoos, food, drinks and more. There will also be passports available for purchase that get you 15 adult beverage samples for $20. All proceeds will go to The Dogtopia Foundation. 

6. Lager & Friends

SATURDAY FROM NOON TO 4 P.M. | OLD HEIDELBERG PARK

Sure, you’ve been to beer festivals, but have you ever been to a lager festival? This event, the first to be in person since the exceptional 2019 festival, showcases the range of the world’s most popular family of beers. There will be big bocks and dark dunkels, but many of the lagers pouring will be light and refreshing. More than 20 breweries will be on hand – many from out of state that don’t normally sell beer in Wisconsin.

A view of the 2019 Lager & Friends beer festival from the Turner Hall balcony. Photo by Chris Drosner

7. Milwaukee Highland Games

SATURDAY FROM 9:00 A.M. TO 9:00 P.M.| CROATIAN PARK

This is not a BYOB – bring your own bagpipes – event. Bagpipe and other traditional Scottish music will be provided. Attendees can watch archery, cricket, highland dancing and more. Children 12 and under get in for free, and tickets for adults are $10. 

8. The Masked Singer

SATURDAY AT 8:00 P.M.| THE RIVERSIDE THEATER

The hit show’s national tour stops in Milwaukee with the promise of a new mystery celebrity being revealed. Fan favorites and new acts will perform. Tickets are available online.

9. MotoAmerica Superbike Series & Vintage MotoFest

ALL WEEKEND | ROAD AMERICA

The all-weekend fest gives enthusiasts a chance to learn how to ride different motorcycles. Fans can even camp out at nearby sites to extend the fun. If you want to participate yourself, you can enter your motorcycle upon arrival Saturday morning between 9-11 a.m. or pre-register online

10. Pridefest

ALL WEEKEND | SUMMERFEST GROUNDS

Pride returns to Milwaukee with flair this summer. Multiple drag shows, comedy acts and musicians are included in the lineup. Lady Gaga fans will enjoy a musical tribute for the musician. Attendees can buy single day admission or a three-day pass.

Photo by Visit Milwaukee

11. John Caparulo at The Laughing Tap

ALL WEEKEND | THE LAUGHING TAP

Comedian John “Cap” Caparulo, who has written for Showtime, ABC, Netfilx and Disney, kicks off a five-show series, at the local comedy bar. Expect laughs and beer. Tickets are $30. 

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