24 Things to Do in Milwaukee This Week · May 21–24, 2026

Festivals & Special Events

Gateway to Asia – Asian Culture Festival featuring AAPI Celebration

A cultural festival celebrating Asian and Pacific Islander heritage with food, performances, and community at Bayshore in Glendale.

Friday, May 22, 2026 11:00 AM · Bayshore, Glendale

BLK Girl Fest: Unapologetically HER

A celebration of Black womanhood featuring community, culture, and empowerment at the Baird Center.

Saturday, May 23, 2026 10:00 AM · Baird Center

Falls Memorial Fest

Free community festival with a 5K walk/run, live music, food, marketplace vendors, and beer and wine gardens.

Saturday, May 23, 2026 11:00 AM · Menomonee Falls area

Music & Nightlife

New Wave Insanity Dance Party at The Cooperage

17th anniversary blowout dance party presented by WMSE 91.7 spinning Bowie, New Order, The Cure, The Clash, and beyond.

Friday, May 22, 2026 · The Cooperage, 822 S. Water St.

Baby Keem – The Ca$ino Tour

Hot-ticket hip-hop show with Baby Keem bringing his Ca$ino Tour to The Rave — selling fast.

Friday, May 22, 2026 8:30 PM · The Rave / Eagles Club

Throwback Prom Night w/ Night Fever & 5 Card Studs

A retro prom-themed dance night with live bands Night Fever and 5 Card Studs — dust off your corsage.

Saturday, May 23, 2026 8:00 PM · The Argo

Food & Drink

Asian Restaurant Week Milwaukee

A week-long celebration of Asian cuisine across Milwaukee with special menus and limited-time dishes at standout local spots.

Friday, May 22, 2026 · Various locations, Milwaukee

War Memorial Beer Garden Opening

The seasonal War Memorial Beer Garden opens for Memorial Day weekend with live music every Friday, Saturday, and Sunday from 1–4pm.

Friday, May 22, 2026 11:00 AM · Veterans Park

Chef's Table: A Pop-Up Dinner

An intimate pop-up dinner experience at The Argo in Whitefish Bay — limited seats, big flavors.

Sunday, May 24, 2026 4:30 PM · The Argo, Whitefish Bay

Downtown Dining Week

Milwaukee Downtown's annual week-long celebration of downtown restaurants with special menus and deals across the city.

Thursday, May 28, 2026 · Downtown Milwaukee

Free Events

Field of Flags Remembrance Ceremony

A Memorial Day remembrance ceremony at Veterans Park amid the iconic Field of Flags display.

Friday, May 22, 2026 11:00 AM · Veterans Park

Line Dancing Night w/ Redd's Line Up

Free line dancing night at The Argo on the North Shore — all levels welcome.

Friday, May 22, 2026 7:00 PM · The Argo

Spring Market Madness – Nothing Over $30

A budget-friendly spring market where every item is $30 or under — shop local on Milwaukee's near west side.

Saturday, May 30, 2026 8:00 AM · 1949 N 39th St, Milwaukee

Family-Friendly

Dan Jansen Family Fest

Annual Memorial Day weekend festival at Konkel Park featuring a 5K, live music, food vendors, and family activities honoring Olympic speed skating champion Dan Jansen.

Friday, May 22, 2026 5:00 PM · Konkel Park, Greenfield

Kid Boogie Down at The Cooperage

The final kid dance party of the season at The Cooperage — morning music, dancing, bubbles, and all-around good vibes for kids and parents.

Sunday, May 31, 2026 10:00 AM · The Cooperage, 822 S. Water St.

Arts & Culture

Jason Cheny at Milwaukee Improv

Stand-up comedy weekend with Jason Cheny headlining five shows at the Milwaukee Improv's Main Room.

Friday, May 22, 2026 · Milwaukee Improv, Main Room

ComedySportz Match

Two teams of improv comedians compete in audience-suggestion-driven games in an all-ages comedy sports format.

Friday, May 22, 2026 7:30 PM · ComedySportz Milwaukee, 420 South 1st Street

Behind the Build: Works in Circulation

A free pop-up art event at House of RAD in the Menomonee Valley showcasing works in progress and circulation.

Saturday, May 23, 2026 1:30 PM · House of RAD, Menomonee Valley

Date Night

Tune Inn at The Outsider Rooftop

Live music, DJ sets, craft cocktails, and small bites on the 9th floor of the Journeyman Hotel — Milwaukee's premier rooftop summer series presented by Bacardi, every Thursday through Sunday.

Friday, May 22, 2026 · The Outsider, Journeyman Hotel

George & Gracie: A Love Story

Milwaukee's Jim Pickering and Tami Workentin bring the heartfelt love story of George Burns and Gracie Allen to life at the intimate Stackner Cabaret.

Saturday, May 23, 2026 7:30 PM · Stackner Cabaret, 108 E. Wells St.

Milwaukee Speed Dating for Singles (Age 27-45)

An almost-full speed dating event for singles ages 27–45 at Milwaukee Brewing & Distilling Company.

Monday, May 25, 2026 8:00 PM · Milwaukee Brewing & Distilling Company

Outdoors & Active

Dog Days at The Argo

A dog-friendly afternoon social at The Argo — bring your pup and enjoy the North Shore vibes.

Sunday, May 24, 2026 1:00 PM · The Argo

Wake N' Bake Yoga Summer Self-Care Soirée at Canni Hemp

MKE Yoga Social kicks off outdoor yoga season in a lanai setting at Canni Hemp, blending movement, wellness vendors, and community self-care.

Saturday, May 30, 2026 · Canni Hemp, Milwaukee

Global Running Day at Zocalo Food Park

Buena Tierra Run Club and New Balance team up for a 3-mile lakefront run and post-run celebration at Zocalo Food Park.

Wednesday, June 3, 2026 6:00 PM · Zocalo Food Park, Milwaukee