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

• Dates: October 3–5

• Location: Henry Maier Festival Park

• 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

• Dates: October 3–26

• Venue: Skylight Music Theatre at the Broadway Theatre Center

• 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

• Dates: October 10, 17, 24, 31

• Time: 7:00 PM – 8:00 PM

• Venue: Manfred Olson Planetarium

• 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

• 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

• Dates: November 1–2

• Location: Wisconsin Center

• For: Model train enthusiasts and families alike

• What to Expect: Explore the world of miniature railroading with interactive displays, workshops, and a vast array of model trains. discovermilwaukee.com

🎭 GalaxyCon Milwaukee

• Dates: November 7–9

• Venue: The Baird Center

• Focus: Pop culture, sci-fi, anime, and cosplay

• Highlights: Meet celebrities, participate in cosplay contests, and immerse yourself in panels and workshops celebrating fandom culture. GalaxyCon

🎤 Comedy at Milwaukee Improv

• Dates: Various dates in November

• Featured Acts:

  Brooks Wheelan: November 1–2
  Funny Marco: November 7–9
  Bob the Drag Queen: November 21–22

• Venue: Milwaukee Improv

• Details: Enjoy a lineup of top-tier comedians bringing laughter to the city. Improv

🎄 Holiday Events Preview

• 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

• Discovery World Museum

  Events: Animal Encounters, Blue Star Welcome Week, and Kohl’s Design It! Lab Open sessions throughout October. Discovery World

• 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