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Bay View Bash, food festivals, and more. Here’s what to do in Milwaukee this weekend.

Elisabeth MontemurrobyElisabeth Montemurro
September 17, 2026, 6:47 am
in Entertainment, What's On Tap, Wisconsin's Morning News
Comedy In Milwaukee, Artists Taking the Stage, and Alternative March Brackets

MILWAUKEE — Looking for the best things to do in Milwaukee and southeastern Wisconsin this weekend? From food and wine on the lakefront and a huge Bay View street festival to world-premiere theater, intimate opera, glass art and even a night devoted to an Italian card game, here are Sandy Maxx’s top picks for September 17 through September 20.

Festivals

Three Pillars Fest

Saturday, September 19 | 11 a.m.-3 p.m. | Three Pillars Woods | Dousman

This free, all-ages festival packs a remarkable amount of fun into four hours. Look for carnival games, a classic car show, craft fair, face painting, a fishing contest, live music, petting zoo, rock-climbing wall and even a roving magician. The centerpiece is the signature Rubber Duck Race fundraiser with 2,000 yellow toys bobbing down the Bark River, making this an especially good pick for grandparents, parents and kids to enjoy together.

Bay View Bash

Saturday, September 19 | 11 a.m.-10 p.m. | Kinnickinnic Avenue, Potter Street to Clement Avenue | Milwaukee

For 11 hours, KK becomes one big celebration of Bay View’s music, food, art and wonderfully distinctive neighborhood personality. Lots of live, local music on several stages. Established in 2004, the Bash also puts its proceeds back into neighborhood nonprofits and community projects.

Freshwater Food & Wine Festival

Saturday-Sunday, September 19-20 | Henry Maier Festival Park | Milwaukee

Come hungry and curious as chefs Dan Jacobs of Top Chef fame, Elena Terry, Adam Pawlak, George Motz, Joe Sasto and Tony “Professor Pizza” Scardino headline a weekend devoted to food, wine and culinary creativity. Watch live demonstrations and cooking competitions, including a Hell’s Kitchen faceoff, sample more than 80 wines representing seven global wine regions, explore Restaurant Row and food trucks, or splurge on experiences including The Flight Deck omakase. Entertainment includes Wisconsin comedian Charlie Berens, DJ Shawna, Sazerac 5, the Extra Crispy Brass Band and more.

On Stage

Maybe We’ll Fly

Opening Weekend | September 18-20 | Milwaukee Chamber Theatre | Milwaukee

Wisconsin art history inspires a brand-new theatrical work as playwright Marie Kohler draws upon legendary Wisconsin outsider artist Mary Nohl and the extraordinary lakeside environment she created. This world-premiere play with music features a score by Tony-nominated composer Josh Schmidt, direction and movement by Elizabeth Margolius and live cello from Alicia Storin.

Trayf

Opening Weekend | September 17-20 | Next Act Theatre | Milwaukee

Two Orthodox Jewish teenage best friends drive a “Mitzvah Tank” through 1990s New York City, hoping to make the world better one good deed at a time. But their friendship is tested when an outsider introduces one of them to rock and roll, roller skates and a wider secular world. Next Act describes Trayf as a funny and heartwarming road-trip bromance exploring youth, faith, friendship and the universal feeling that you don’t quite fit in.

Pagliacci

Friday-Sunday, September 18-20 | Inspiration Studios | West Allis

Think opera isn’t for you? Brew City Opera’s intimate Pagliacci might change your mind. A traveling performer discovers his wife’s infidelity just before curtain, and the comedy they’re supposed to perform begins colliding with real-life jealousy, rage and tragedy. The roughly 90-minute production, performed in English with some original Italian, brings audiences close to the singers and the drama rather than placing the action on a distant opera-house stage.

Sing Along

Pat McCurdy

Friday, September 18 | 8 p.m. | The Argo | Whitefish Bay

A Pat McCurdy show isn’t something you simply sit and watch. The longtime Milwaukee favorite mixes original songs, quick-witted comedy and plenty of audience participation into a show his fans know well enough to sing and dance along with. There’s also a community connection: $1 from every ticket supports local artist mental health and well-being.

Art in Action

Midwest Glass Art Expo

Saturday-Sunday, September 19-20 | Washington County Fair Park & Conference Center | West Bend

Watch glass art take shape during the first Midwest Glass Art Expo, bringing artists, makers, suppliers and collectors together in West Bend. Visitors can see live glass demonstrations, meet makers and explore supplies and finished artwork. Want to do more than watch? Separately ticketed workshops offer hands-on opportunities to create projects including glass bouquets and fused-glass landscapes.

Sweeping the Cards

Italian Community Center Scopa Night

Friday, September 18 | Italian Community Center | Milwaukee

Try your hand at Scopa, the traditional Italian card game whose name means “sweep.” Played with a 40-card Italian deck, the strategy-and-memory game challenges players to capture or “sweep” cards from the table while racing to reach 11 points. Scopa Night offers a casual opportunity to learn, play, socialize and enjoy concessions at Milwaukee’s Italian Community Center.

Comedy

Two Brothers One Mind Live Adult Comedy & Magic Show

Thursday, September 17 | 7 p.m. | The Laughing Tap | Milwaukee

Why choose between comedy and magic? Milwaukee’s Two Brothers One Mind bring both to The Laughing Tap for an adults-only Thursday night show. The duo has been voted Best Magicians in Milwaukee, appeared on America’s Got Talent and is set to appear on The CW’s Masters of Illusion. Madison magician Matthew Teague, who has appeared on Penn & Teller: Fool Us, adds another dose of illusion to the evening.

Keep up with culture and creativity in Wisconsin and around the world with “What’s On Tap with Sandy Maxx” weekdays at 6 p.m. on WTMJ.

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Tags: Bay ViewCedarburgFreshwater Food & Wine FestivalHenry Maier Festival ParkItalian Community CenterMilwaukeeMilwaukee Chamber TheaterNext Act TheatreThe ArgoWest AllisWest BendWhitefish Bay

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