Your Ultimate Guide to Milwaukee’s Fall Events: October & November 2025
Planning a getaway to Milwaukee this fall? From vibrant festivals to cozy indoor experiences, Milwaukee’s event calendar is packed with activities that cater to every interest. Whether you’re a foodie, music lover, family traveler, or culture enthusiast, here’s your curated guide to the must-see events in Milwaukee for October and November 2025.
🍂 October 2025: Fall into Milwaukee’s Festive Spirit
🎃 Milwaukee Oktoberfest
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Dates: October 3–5
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Location: Henry Maier Festival Park
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Highlights: Celebrate Bavarian culture with authentic German beer, bratwurst, live polka music, and family-friendly activities. This year’s festival returns to the lakefront, offering a festive atmosphere with stunning views. Milwaukee Oktoberfest
🎨 Fiddler on the Roof
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Dates: October 3–26
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Venue: Skylight Music Theatre at the Broadway Theatre Center
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Experience: A poignant rendition of the classic musical, featuring two violins owned and played before and during the Holocaust, adding a deep historical context to the performance. milwaukeemag.com
🌌 Creepy Cosmos
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Dates: October 10, 17, 24, 31
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Time: 7:00 PM – 8:00 PM
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Venue: Manfred Olson Planetarium
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Details: Embark on a spooktacular journey through the eerie parts of space, featuring indoor stargazing sessions and chilling cosmic tales. milwaukeemag.com
🎶 Live Music & Concerts
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Home Free Vocal Band
Date: October 23
Venue: Pabst Theater
Genre: Country a cappella -
Colin Hay
Date: October 31
Venue: Pabst Theater
Genre: Alternative Rock -
Candlelight Concerts
Dates: Various dates in October
Highlights: Intimate classical performances in candlelit settings, including tributes to Hans Zimmer and Vivaldi’s Four Seasons. milwaukee-theatre.com
🍁 November 2025: Embrace the Cozy Vibes
🚂 Trainfest 2025
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Dates: November 1–2
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Location: Wisconsin Center
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For: Model train enthusiasts and families alike
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What to Expect: Explore the world of miniature railroading with interactive displays, workshops, and a vast array of model trains. discovermilwaukee.com
🎭 GalaxyCon Milwaukee
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Dates: November 7–9
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Venue: The Baird Center
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Focus: Pop culture, sci-fi, anime, and cosplay
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Highlights: Meet celebrities, participate in cosplay contests, and immerse yourself in panels and workshops celebrating fandom culture. GalaxyCon
🎤 Comedy at Milwaukee Improv
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Dates: Various dates in November
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Featured Acts:
Brooks Wheelan: November 1–2
Funny Marco: November 7–9
Bob the Drag Queen: November 21–22 -
Venue: Milwaukee Improv
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Details: Enjoy a lineup of top-tier comedians bringing laughter to the city. Improv
🎄 Holiday Events Preview
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Pabst Theater 50th Anniversary Production
Dates: November 25–December 24
Venue: Pabst Theater
What to Expect: A festive production marking the theater’s 50th anniversary, setting the stage for the holiday season. milwaukeerep.com
👨👩👧👦 Family-Friendly Activities
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Discovery World Museum
Events: Animal Encounters, Blue Star Welcome Week, and Kohl’s Design It! Lab Open sessions throughout October. Discovery World
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Estabrook Beer Garden
Dates: Open until November 2
Activities: Enjoy live music and a cozy atmosphere by the river, perfect for families and groups. discoverthenorthshoremke.com