20 Things to Do in Milwaukee This Week · September 24–27, 2026

Free Events

Fitness on the Plaza at Deer District

Free outdoor fitness event at the Deer District plaza.

Thursday, September 24, 2026 6:00 PM · Deer District, Milwaukee

Riverwest Jazz Fest

Free multi-venue jazz festival featuring multiple groups performing throughout the night across Riverwest.

Friday, September 25, 2026 6:00 PM · Riverwest, Milwaukee

Music & Nightlife

Big Shrimp at The Cooperage

High-octane progressive improvised rock quartet Big Shrimp makes their Harborfront debut at The Cooperage, blending danceable funk, exploratory rock, and fearless improvisation.

Thursday, September 24, 2026 · The Cooperage, Milwaukee

Bubba Dub at Milwaukee Improv

Stand-up comedian Bubba Dub headlines two shows at the Milwaukee Improv.

Friday, September 25, 2026 7:00 PM · Milwaukee Improv, Milwaukee

House Circuit at Ivanhoe Plaza

House Circuit brings Chicago selector Ivano Lima and Milwaukee legend Moorhaus to iconic Ivanhoe Plaza for an evening of house music and golden-hour energy.

Saturday, September 26, 2026 · Ivanhoe Plaza, Milwaukee

Drunken Jukebox 9th Anniversary

Drunken Jukebox celebrates 9 years with Milwaukee improvisers performing improvised songs and scenes inspired by audience suggestions — uncensored 18+ show.

Saturday, September 26, 2026 8:00 PM · ComedySportz Milwaukee, 420 S 1st Street

Kota The Friend at The Rave

Kota The Friend brings the Just Happy To Be Here Tour to The Rave, joined by NilexNile and Ace Parker.

Saturday, September 26, 2026 8:00 PM · The Rave / Eagles Club, Milwaukee

Festivals & Special Events

2nd Annual Mi Gente Mercado! A Hispanic Heritage Month Pop-Up Market

Second annual Hispanic Heritage Month pop-up market celebrating community and culture at The Sugar Maple.

Saturday, September 26, 2026 12:00 PM · The Sugar Maple, Milwaukee

Milwaukee Oktoberfest

Milwaukee's annual Oktoberfest celebration with beer, food, live music, and special events at Henry Maier Fest Park — free admission the first hour of each day.

Friday, October 2, 2026 Fri 4-10PM, Sat 11AM-10PM, Sun 11AM-6PM · Henry Maier Fest Park, Milwaukee

Outdoors & Active

Deep Focus Restorative Yoga

Weekly restorative yoga class in Bayview at Wild Workouts & Wellness studio.

Saturday, September 26, 2026 9:30 AM · 3056 S Delaware Ave, Milwaukee (Bayview)

Full Moon Beach Yoga + Sound Journey

Pay-what-you-can full moon yoga and sound journey on Bayview Beach with movement, community, and recovery under the full moon.

Saturday, September 26, 2026 5:30 PM · Bayview Beach, Milwaukee

Full Moon Beach Yoga (Atwater Beach)

Evening of movement, community, and recovery under the full moon at Atwater Beach, with optional 1K walk, 5K run, or Zumba followed by yoga.

Sunday, September 27, 2026 4:30 PM · Atwater Beach, Milwaukee

Arts & Culture

MAYBE WE'LL FLY World Premiere

World premiere musical by Marie Kohler with music by Josh Schmidt, running through October 11 at Broadway Theatre Center's Studio Theatre.

Thursday, September 24, 2026 · Broadway Theatre Center, Studio Theatre, Milwaukee

Trayf at Next Act Theatre

Funny and heartwarming road-trip bromance about Orthodox Jewish teens navigating youth, identity, and friendship — running through the weekend at Next Act Theatre.

Friday, September 25, 2026 7:30 PM · Next Act Theatre, 255 S Water St, Milwaukee

Arts @ Large 25th Anniversary Community Celebration

Free community celebration marking Arts @ Large's 25th anniversary at 1100 S 5th St.

Saturday, October 3, 2026 1:00 PM · 1100 S 5th St, Milwaukee

Family-Friendly

Patiopalooza at The Little Village Play Cafe

Family-friendly outdoor patio event at The Little Village Play Cafe.

Thursday, September 24, 2026 4:00 PM · The Little Village Play Cafe, Milwaukee

China Lights 2026: Legends Come Alive at Boerner Botanical Garden

Stunning lantern festival featuring master-crafted light sculptures spanning Chinese tradition, enchanted ocean, and fantasy worlds at Boerner Botanical Garden.

Friday, September 25, 2026 5:30 PM · Boerner Botanical Garden, 9400 Boerner Drive, Hales Corners

ComedySportz Match

Two improv comedy teams compete in audience-suggested games — a hilarious, all-ages show at ComedySportz Milwaukee.

Friday, September 25, 2026 7:30 PM · ComedySportz Milwaukee, 420 S 1st Street

Food & Drink

HOT Yoga-lattes Pop-Up

A pop-up combining hot yoga and lattes at Healium Hot Yoga in Bay View.

Friday, September 25, 2026 12:00 PM · Healium Hot Yoga-Bay View, Milwaukee

Date Night

Tune Inn Live Music & DJ Sets at The Outsider Rooftop

Curated live music and DJ sets on Milwaukee's favorite rooftop, The Outsider, with Bacardi cocktails — Thursdays through Sundays all season.

Thursday, September 24, 2026 7:30 PM · The Outsider Rooftop, Milwaukee