15 Things to Do in Milwaukee This Weekend: Sept. 24-27

15 Things to Do in Milwaukee This Weekend: Sept. 24-27

As the summer fades, Milwaukee still offers plenty of fun events. This weekend, you’ll find a documentary festival, waterside festival, symphonic celebration of soul and much more.

Featured Events 

1. Milwaukee Film’s Dialogues Documentary Festival

ALL WEEKEND | ORIENTAL AND DOWNER THEATERS

Check out four days worth of screenings and filmmaker Q&As at Milwaukee Film’s third annual celebration of documentary filmmaking. The documentaries on show take on timely topics, from AI to natural disasters, and Heavy Is the Crown (screening Sept. 27 at the Oriental) follows Milwaukee community activist Vaun Mayes. Peruse the full lineup of screenings here. Individual tickets can be purchased online and general public admission passes are also available for $80.   

2. Doors Open

SATURDAY AND SUNDAY | MULTIPLE LOCATIONS

This weekend more than 100 often closed-to-the-public Milwaukee spots, from the industrial to the historic to the just plain weird, will open for exclusive tours. That includes industrial factories, churches, art galleries and even a sewer manhole. For a full list of Doors Open events, click here. 

3. South Side Dining Week Preview

SUNDAY FROM 12-4 P.M. | ZÓCALO FOOD PARK

Visit Zócalo Food Park ahead of South Side Dining Week, which runs from Sept. 27-Oct. 3, to get a taste of the flavors on offer all week long. The free preview event will feature complimentary samples from Tres Hermanos, El Tlaxcalteca, Los Gemelos Tacosa and Sabor a Pueblo Restaurant and Bakery. You can also catch an interactive chef demonstration by Chefs Latinos Wisconsin, live music and more. And then, during South Side Dining Week, you can grab limited-time dishes and specials from local restaurants. Find the full list of participating spots here.


If someone has inspired you through their service, leadership or dedication, the Unity Awards are your opportunity to recognize them!

 

Other Events

4. Mapping Racism and Resistance in Milwaukee County

THURSDAY FROM 6-7:30 P.M. | CHRIST CHURCH EPISCOPAL

Join UW-Milwaukee professors Anne Bonds and Derek Handley to hear their findings based on research and tracking done by citizens across Milwaukee. Their goal is to create the first comprehensive map of racial covenants within the city, while analyzing and visualizing the historical geographies and Black resistance movements. They’ll be discussing what they’ve learned so far and what comes next in their project. The talk is free to attend and an RSVP is open online. 

5. Bay View Gallery Night

FRIDAY FROM 5-10 P.M. | BAY VIEW NEIGHBORHOOD

Support local artists, musicians and small businesses at this event highlighting Bay View’s vibrant community. Events throughout the neighborhood include art showings, makers markets and more – find a full list here. Gallery Night is free, open to the public and family-friendly. 

6. Opening Night of Gypsy: A Musical Fable

FRIDAY AT 7:30 P.M. | SKYLIGHT MUSIC THEATRE

The fall season at Skylight kicks off with Gypsy, a broadway classic exploring the final years of American Vaudeville. The show – which runs through Oct. 18 – follows Momma Rose and her daughters as they try to succeed in the brutal world of show business. Tickets are on sale online. 

7. UWM Makers Market

SATURDAY FROM 10 A.M.-5 P.M. | SPAIGHTS PLAZA AT UW-MILWAUKEE

For the first time, UW-Milwaukee is hosting a makers market, selling goods from more than 50 students, alumni and community members. The market will fill Spaights Plaza with artisanal foods, handcrafted jewelry, original artwork and more. A food truck and live music will also enliven the scene. 

8. MILK Fest 2026

SATURDAY FROM 11 A.M.-5 P.M. | 3RD ST. MARKET HALL

MILK aka the “Milwaukee Indie Local Comic” fest is back this weekend! The show features local artists as well as artists from around the Midwest. The festival provides an opportunity for community members to get to know independent comic artists and illustrators, ask questions and purchase original art. This event is free to attend and open to all ages. 

9. Kings of Soul

SATURDAY AND SUNDAY | BRADLEY SYMPHONY CENTER

The Milwaukee Symphony Orchestra opens its Pops season with this showcase of classic soul. You’ll hear the greatest hits from artists including Marvin Gaye, James Brown, The Temptations, Curtis Mayfield and more.  

10. Milwaukee World Oddities Expo

SATURDAY AND SUNDAY FROM 11 A.M.-7 P.M. | BAIRD CENTER

Milwaukee’s “peculiar paradise” is back and bigger than ever. Check out all things weird as vendors, artists and performers combine art, history, science and entertainment into an expo full of the unusual. A single day general admission ticket costs $20 with the potential for add on classes and exhibition access. 

11. The Low Down Block Party

SATURDAY FROM 12-8 P.M. | INDEED BREWING COMPANY

Get the low down at Indeed Brewing Company’s Low Down Block Party. Indeed is shutting down their block in Walker’s Point to serve food, showcase local vendors, play live music and pour some of their craft beer, of course. At the end of the night, head to the rooftop bar for a silent disco afterparty. This event is free to attend. 

12. Third Space Brewing 10th Anniversary Party

SATURDAY FROM 12 P.M.-10 P.M. | THIRD SPACE BREWING

In honor of Third Space reaching a decade in business, the local brewery is throwing a party packed with live music, food trucks, a stein hoisting competition and more. Unite the Clans, a Scottish-style rye ale, is returning “from the archives” and Third Space is also releasing Super Happy, a new take on the fan favorite Happy Place pale ale. 

13. Harbor Fest

SUNDAY FROM 11 P.M.-3 P.M. | HARBOR VIEW PLAZA

Want to get out on the harbor before the weather really gets cold? Take your opportunity at this festival, which includes free boat rides through the city waterways. It’s the 10th anniversary of this riverside event, which also includes food trucks and the chance to release a baby sturgeon into the harbor.

14. Forks & Futures

SUNDAY FROM 11:30 A.M.-2:30 P.M. | WOMAN’S CLUB OF WISCONSIN

Join FoodRight in their first-ever Forks and Futures, bringing together professional chefs, student chefs and community leaders for a brunch benefiting culinary nutrition education. This Sunday, six Milwaukee chefs – including Justin Aprahamian of Sanford, Dana Spandet of Flour Girl & Flame, and Gregory León of Amilinda – will cook alongside FoodRight students to serve an elevated brunch to guests. Throughout the morning, hear inspiring stories from FoodRight’s students and their families and participate in a live and silent auction. All proceeds go to funding Milwaukee youth nutrition and cooking education. Tickets are $180 reach and tables of up to 10 are available. 

15. Bean Plant Block Party

SUNDAY AT 12 P.M. | ANODYNE COFFEE, WALKER’S POINT

Anodyne is celebrating its fifth annual Bean Plant Block Party outside its Bruce Street location this Sunday. The day will feature skateboard ramps and obstacles, beer from Indeed Brewing, vintage curators and local makers, live performances, food trucks and more. This event is free and open to all ages. Skaters of all skill levels are encouraged to participate in the fun.